Substituted 4-cyano-3-phenyl-4-(pyridin-3-yl)butanoates, processes for preparation thereof and use thereof as herbicides and plant growth regulators

ABSTRACT

Compounds of the formula (I) or salts thereof, 
     
       
         
         
             
             
         
       
     
     in which (R 1 ) m , (R 2 ) n , R 3  and R 4  as defined in Claim  1  are suitable as herbicides for the control of harmful plants or as plant growth regulators. 
     The compounds can be prepared by the processes of Claim  7.

The invention relates to the technical field of the herbicides and plant growth regulators, preferably the herbicides for controlling unwanted vegetation or the herbicides for the selective control of broad-leaved weeds and weed grasses in crops of useful plants, or the plant growth regulators which can be used for influencing the growth of crop plants.

In their application, crop protection agents known to date for the selective control of harmful plants in crops of useful plants or active compounds for controlling unwanted vegetation sometimes have disadvantages, be it (a) that they have no or else insufficient herbicidal activity against particular harmful plants, (b) that the spectrum of harmful plants which can be controlled with an active compound is not wide enough, (c) that their selectivity in crops of useful plants is too low and/or (d) that they have a toxicologically unfavorable profile. Furthermore, some active compounds which can be used as plant growth regulators for a number of useful plants cause unwanted reduced harvest yields in other useful plants or are not compatible with the crop plant, or only within a narrow application rate range. Some of the known active compounds cannot be produced economically on an industrial scale owing to precursors and reagents which are difficult to obtain, or they have only insufficient chemical stabilities. In the case of other active compounds, the activity is too highly dependent on environmental conditions, such as weather and soil conditions.

The published patent applications EP-A-5341, EP-A-266725, EP-A-270830, JP-04/297454, JP-04/297455, JP-05/058979, WO 2011/003775, WO 2011/003776, WO 2011/042378, WO 2011/073143 and WO2011/098417 disclose herbicidal cyanobutyrates.

EP-A-5341 describes herbicidal esters and amides of 4-cyano-3,4-diarylbutanoic acids. The aryl radicals mentioned are optionally substituted phenyl radicals and unsubstituted pyridyl or thienyl. The specific examples include mainly 4-cyano-3,4-diphenylbutanoic acids and esters. There are two specific examples of compounds containing pyridyl, namely 4-cyano-4-phenyl-4-(pyridin-3-yl)butanoic acid and the corresponding ethyl ester.

According to EP-A-5341, the threo isomers are generally suitable for the non-selective control of harmful plants, whereas the erythro/threo isomer mixtures are suitable for the selective control of harmful plants in some crops of useful plants. Moreover, EP-A-5341 mentions that the 2 enantiomers belonging to the threo form differ in their activities, which was studied in an exemplary manner using the different activities of the enantiomers of the enantiomer pair of 4-cyano-3,4-diphenylbutanoic acid having unsubstituted phenyl radicals.

EP-A-266725 discloses a number of erythro/threo isomer mixtures of 4-cyano-3,4-diphenylbutanoic acids and derivatives thereof which can be used for the selective control of weeds in rice crops.

EP-A-270830 describes that threo isomers and erythro/threo isomer mixtures of 4-cyano-3,4-diarylbutanoic acid (esters) can be used as plant regulators, preventing the development of an infructescence in various harmful grasses. The aryl radicals mentioned are optionally substituted phenyl radicals and unsubstituted pyridyl or halogen-substituted pyridyl. Specific examples relate mainly to (substituted) 4-cyano-3,4-diphenylbutanoic acid (esters). Additionally described are also 4-cyano-3-pyridyl-4-phenylbutanoic acid esters, such as the compound ethyl 4-cyano-3-pyridyl-4-phenylbutanoate, or 4-cyano-3-phenyl-4-pyridylbutanoic acid ester, such as the compound methyl 4-cyano-3-(4-chlorophenyl)-4-(6-fluoropyridin-3-yl)butanoate. JP-04/297455 discloses herbicidal 4-cyano-3-phenyl-4-heteroarylbutanoic acid (esters), where the heterocyclic radicals are selected from the group consisting of 1,2,4-triazolyl, 1-pyrazolyl, 1-imidazolyl, 2- and 3-thienyl, 2- and 3-pyridyl, 1-methylpyrrol-2-yl, 2-quinolinyl, 2-methyl-3-trifluoromethylpyrazol-5-yl and 5-trifluoromethylpyridin-2-yl. Specific compounds from the 3-pyridyl series only comprise unsubstituted pyridin-3-yl radicals, for example the compounds propargyl and allyl 4-cyano-3-phenyl-4-(pyridin-3-yl)butanoate.

WO 2011/003775 discloses specific esters of 4-cyano-3,4-diphenylbutanoic acids which can be used as effective herbicides, preferably also in crops of useful plants. WO 2011/003776, WO 2011/042378, WO 2011/073143 and WO2011/098417 disclose 4-cyano-3,4-diphenylbutanoic acids and esters which have specific substitutions at the phenyl radicals and can be used as effective herbicides, preferably also in crops of useful plants.

The herbicidal activity of the known compounds of the class of substances mentioned, in particular at low application rates, and/or their compatibility with crop plants, remain deserving of improvement.

For the reasons mentioned, there is still a need for alternative, highly active herbicides for the selective application in plant crops or use on non-crop land. It is also desirable to provide alternative chemical active compounds which may be used in an advantageous manner as herbicides or plant growth regulators.

Likewise desirable are compounds having herbicidal activity which are highly effective against economically important harmful plants even at relatively low application rates and can be used selectively in crop plants, preferably with good activity against harmful plants.

Surprisingly it has now been found that certain heterocyclically substituted cyanobutyrates have particular herbicidal activities and can preferably be employed in some crops selectively for controlling harmful plants.

The present invention provides compounds of the formula (I) or salts thereof

in which

-   (R¹)_(m) represents m substituents R¹, -    where R¹, if m=1, or each of the substituents R¹, if m is greater     than 1, independently of the others represents halogen, cyano,     nitro, hydroxy, (C₁-C₈)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,     (C₁-C₈)-alkoxy, (C₁-C₈)-alkylthio, (C₁-C₈)-alkylsulphinyl,     (C₁-C₈)-alkylsulphonyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-haloalkoxy,     (C₁-C₆)-haloalkylthio, (C₁-C₆)-haloalkylsulphinyl,     (C₁-C₆)-haloalkylsulphonyl, (C₂-C₆)-haloalkenyl,     (C₂-C₆)-haloalkynyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl,     (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl which is     optionally substituted by one or more radicals from the group     consisting of halogen and (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkoxy which     is optionally substituted by one or more radicals from the group     consisting of halogen and (C₁-C₄)-alkyl, or a radical of the formula     C(O)OR⁵, C(O)NR⁶R⁷, C(O)-Het¹, NR⁸R⁹ or Het² -    or where in each case two groups R¹ located ortho at the ring or R¹     and R³ together represent a group of the formula —Z¹-A*-Z² in which     -   A* represents an alkylene group having 1 to 4 carbon atoms which         is optionally substituted by one or more radicals from the group         consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,         (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy,     -   Z¹ represents a direct bond, O or S and     -   Z² represents a direct bond, O or S, -    where the group —Z¹-A*-Z² together with the carbon atoms, attached     to the group, of the phenyl ring form a fused-on 5- or 6-membered     ring, -   (R²)_(n) represents n substituents R², -    where R², if n=1, or each of the substituents R², if n is greater     than 1, independently of the others represents halogen, cyano,     nitro, hydroxy, (C₁-C₈)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,     (C₁-C₈)-alkoxy, (C₁-C₈)-alkylthio, (C₁-C₈)-alkylsulphinyl,     (C₁-C₈)-alkylsulphonyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-haloalkoxy,     (C₁-C₆)-haloalkylthio, (C₁-C₆)-haloalkylsulphinyl,     (C₁-C₆)-haloalkylsulphonyl, (C₂-C₆)-haloalkenyl,     (C₂-C₆)-haloalkynyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl,     (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl which is     optionally substituted by one or more radicals from the group     consisting of halogen and (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkoxy which     is optionally substituted by one or more radicals from the group     consisting of halogen and (C₁-C₄)-alkyl, or a radical of the formula     C(O)OR¹⁰, C(O)NR¹¹R¹², C(O)-Het³, NR¹³R¹⁴ or Het⁴ -    or where in each case two groups R² located ortho at the ring     together are a group of the formula —Z³-A**-Z⁴ in which     -   A** represents an alkylene group having 1 to 4 carbon atoms         which is optionally substituted by one or more radicals from the         group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,         (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy,     -   Z³ represents a direct bond, O or S and     -   Z⁴ represents a direct bond, O or S, -    where the group —Z³-A**-Z⁴ together with the carbon atoms, attached     to the group, of the phenyl ring form a fused-on 5- or 6-membered     ring, -   R³ represents halogen, cyano, nitro, hydroxy, (C₁-C₈)-alkyl,     (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₁-C₈)-alkoxy, (C₁-C₈)-alkylthio,     (C₁-C₈)-alkylsulphinyl, (C₁-C₈)-alkylsulphonyl, (C₁-C₆)-haloalkyl,     (C₁-C₆)-haloalkoxy, (C₁-C₆)-haloalkylthio,     (C₁-C₆)-haloalkylsulphinyl, (C₁-C₆)-haloalkylsulphonyl,     (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl,     (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkyl,     (C₃-C₆)-cycloalkyl which is optionally substituted by one or more     radicals from the group consisting of halogen and (C₁-C₄)-alkyl,     (C₃-C₆)-cycloalkoxy which is optionally substituted by one or more     radicals from the group consisting of halogen and (C₁-C₄)-alkyl, or     a radical of the formula C(O)OR¹⁵, C(O)NR¹⁶R¹⁷, C(O)-Het⁵, NR¹⁸R¹⁹     or Het⁶, -   R⁴ represents hydrogen or a hydrolyzable radical, preferably -    R⁴ represents hydrogen or an optionally substituted hydrocarbon     radical or an optionally substituted heterocyclyl radical, where     each of the two last-mentioned carbon-containing radicals including     substituents has 1 to 30 carbon atoms, preferably 1 to 24 carbon     atoms, in particular 1 to 20 carbon atoms, or     -   R⁴ represents a radical of the formula SiR^(a)R^(b)R^(c),         —NR^(a)R^(b) or —N═CR^(c)R^(d), where in the 3 last-mentioned         formulae each of the radicals R^(a), R^(b), R^(c) and R^(d)         independently of the others represents hydrogen or an optionally         substituted hydrocarbon radical, where, however, SiH₃ for         SiR^(a)R^(b)R^(c) is excluded, or R^(a) and R^(b) together with         the nitrogen atom of the group —NR^(a)R^(b) represent a 3- to         9-membered heterocycle which, in addition to the nitrogen atom,         may contain one or two further ring heteroatoms from the group         consisting of N, O and S and which is unsubstituted or         substituted, or R^(c) and R^(d) together with the carbon atom of         the group —N═CR^(c)R^(d) represent a 3- to 9-membered         carbocyclic radical or a heterocyclic radical which may contain         1 to 3 ring heteroatoms from the group consisting of N, O and S,         where the carbocyclic or heterocyclic radical is unsubstituted         or substituted,     -    where each of the radicals R^(a), R^(b), R^(c) and R^(d)         including substituents has up to 30 carbon atoms, preferably up         to 24 carbon atoms, in particular up to 20 carbon atoms, or     -   R⁴ represents a radical of the formula —C(═O)—R^(e) or         —P(═O)(R^(f))₂, where R^(e) and the radicals R^(f) independently         of one another each represent hydrogen, OH, (C₁-C₈)-alkyl,         (C₁-C₄)-haloalkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl,         (C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₈)-alkyl,         (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkoxy-(C₁-C₈)-alkyl,         (C₃-C₈)-alkenyloxy, (C₃-C₈)-alkenyloxy-(C₁-C₈)-alkyl,         (C₃-C₈)-alkynyloxy, (C₃-C₈)-alkynyloxy-(C₁-C₈)-alkyl, —NR*R**,         with R* and R** being defined below, tri-[(C₁-C₄)-alkyl]silyl,         tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₈)alkyl, (C₃-C₆)-cycloalkyl,         (C₃-C₆)-cycloalkyl-(C₁-C₈)-alkyl, (C₅-C₆)-cycloalkenyl,         (C₅-C₆)-cycloalkenyl-(C₁-C₈)-alkyl, (C₅-C₆)-cycloalkynyl,         (C₅-C₆)-cycloalkynyl-(C₁-C₈)-alkyl, phenyl,         phenyl-(C₁-C₈)-alkyl, phenoxy, phenoxy-(C₁-C₈)-alkyl,         phenylamino, phenylamino-(C₁-C₈)-alkyl, a radical Het⁷,         Het⁷-(C₁-C₆)-alkyl or Het⁷-O—(C₁-C₆)-alkyl,         -   where each of the 15 last-mentioned radicals is             unsubstituted in the acyclic moiety or substituted by one or             more identical or different radicals R^(A) and is             unsubstituted in the cyclic moiety or substituted by one or             more identical or different radicals R^(B), -   R⁵, R¹⁰ and R¹⁵ independently of one another each represent     hydrogen, (C₁-C₆)-alkyl, (C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl,     (C₃-C₆)-halocycloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl,     (C₂-C₄)-alkynyl or the group M mentioned below, preferably     (C₁-C₄)-alkyl, -   R⁶, R⁷, R⁸, R⁹, R¹¹, R¹², R¹³, R¹⁴, R¹⁶, R¹⁷, R¹⁸ and R¹⁹     independently of one another each represent hydrogen, (C₁-C₆)-alkyl,     (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, where each of the 3     last-mentioned radicals independently of the others is unsubstituted     or substituted by one or more radicals from the group consisting of     halogen, nitro, cyano and phenyl which is optionally substituted,     preferably unsubstituted or substituted by one or more radicals from     the group consisting of halogen, nitro, cyano, (C₁-C₄)-alkyl and     (C₁-C₄)-haloalkyl, or (C₃-C₆)-cycloalkyl or phenyl, where each of     the 2 last-mentioned radicals in each case independently of the     other is unsubstituted or substituted by one or more radicals from     the group consisting of halogen, nitro, cyano, (C₁-C₄)-alkyl,     (C₁-C₄)-haloalkyl, phenyl and benzyl, where each of the 2     last-mentioned radicals is optionally substituted, preferably     unsubstituted or substituted by one or more radicals from the group     consisting of halogen, nitro, cyano, (C₁-C₄)-alkyl and     (C₁-C₄)-haloalkyl, -   Het¹, Het², Het³, Het⁴, Het⁵ and Het⁶ independently of one another     each represent a saturated or partially unsaturated radical of a     heterocycle having 3 to 9 ring atoms and at least one nitrogen atom     as ring heteroatom at position 1 of the ring and optionally 1, 2 or     3 further ring heteroatoms from the group consisting of N, O and S,     where the radical of the heterocycle at the nitrogen atom in     position 1 of the ring is attached to the remainder of the molecule     of the compound of the formula (I) and where the heterocycle is     unsubstituted or substituted by one or more radicals from the group     consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,     (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio and oxo,     preferably the radical of a saturated heterocycle of the type     mentioned, in particular a morpholino, piperidino or pyrrolidino     group, -   Het⁷ independently of the others in each case represents a     saturated, partially unsaturated or heteroaromatic monocyclic     heterocyclyl radical having 3 to 9 ring atoms or a 9- or 10-membered     bicyclic heterocycle, each containing 1, 2, 3 or 4 heteroatoms     selected from the group consisting of O, N and S, -   R*, R** independently of one another (and also independently of     other radicals NR*R**) each represent H, (C₁-C₈-alkyl,     (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,     (C₁-C₆)-alkanoyl, [(C₁-C₄)-haloalkyl]carbonyl,     [(C₁-C₄)-alkoxy]carbonyl, [(C₁-C₄)-haloalkoxy]carbonyl,     (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl, phenyl,     phenyl-(C₁-C₄)-alkyl, where each of the 4 last-mentioned radicals is     optionally substituted in the cycle by one or more identical or     different radicals from the group consisting of halogen,     (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy and     (C₁-C₄)-haloalkoxy or, in the case of saturated or partially     unsaturated cyclic base groups, also oxo, or -   R* and R** together with the nitrogen atom represent a 3- to     8-membered heterocycle which, in addition to the nitrogen atom, may     contain one or two further ring heteroatoms from the group     consisting of N, O and S and which may be unsubstituted or     substituted by one or more radicals from the group consisting of     (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo, -   R^(A) represents halogen, cyano, hydroxy or (C₁-C₆)-alkoxy, -   R^(B) represents halogen, cyano, hydroxy, oxo, nitro, (C₁-C₈)-alkyl,     (C₁-C₆)-haloalkyl, cyano-(C₁-C₆)-alkyl, hydroxy-(C₁-C₆)-alkyl,     nitro-(C₁-C₆)-alkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-haloalkenyl,     (C₂-C₈)-alkynyl, (C₂-C₈)-haloalkynyl, (C₁-C₈)-alkoxy,     (C₂-C₈)-alkenyloxy, (C₂-C₈)-alkynyloxy, (C₁-C₈)-haloalkoxy,     (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkoxy,     (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkoxy,     (C₁-C₈)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio,     (C₁-C₈)-alkylsulphinyl, (C₁-C₆)-haloalkylsulphinyl,     (C₁-C₈)-alkylsulphonyl, (C₁-C₆)-haloalkylsulphonyl, a radical of the     formula R^(aa)—C(═O)—, R^(aa)—C(═O)—(C₁-C₆)alkyl, the radicals     R^(aa) being defined below, —NR*R**, R* and R** being defined below,     tri-[(C₁-C₄)-alkyl]silyl, tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₆)-alkyl,     (C₃-C₈)-cycloalkyl, (C₃-C₈)-cycloalkoxy,     (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkyl, (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkoxy,     phenyl, phenyl-(C₁-C₈)-alkyl, phenoxy, phenoxy-(C₁-C₈)-alkyl,     phenylamino, phenylamino-(C₁-C₈)-alkyl or a 5- or 6-membered     monocyclic or 9- or 10-membered bicyclic heterocycle which contains     1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N     and S, where each of the 11 last-mentioned radicals is optionally     substituted in the cyclic moiety by one or more identical or     different radicals R^(bb), -   R^(aa) independently of one another each represent hydrogen, OH,     (C₁-C₈)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl,     (C₁-C₈)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,     (C₁-C₆)-alkoxy-(C₁-C₆)-alkyloxy, (C₁-C₆)-haloalkoxy,     (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkoxy,     (C₃-C₈)-alkenyloxy, (C₃-C₈)-alkenyloxy-(C₁-C₆)-alkyl,     (C₃-C₈)-alkenyloxy-(C₁-C₆)-alkoxy, (C₃-C₈)-alkynyloxy,     (C₃-C₈)-alkynyloxy-(C₁-C₆)-alkyl, (C₃-C₈)-alkynyloxy-(C₁-C₆)-alkoxy,     —NR*R*, where R* and R** are as defined above,     tri-[(C₁-C₄)alkyl]silyl, tri-[(C₁-C₄)alkyl]silyl-(C₁-C₆)-alkyl,     tri-[(C₁-C₄)alkyl]silyl-(C₁-C₆)-alkoxy, (C₃-C₈)-cycloalkyl,     (C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkyl,     (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkoxy, (C₅-C₈)-cycloalkenyl,     (C₅-C₈)-cycloalkenyl-(C₁-C₆)-alkyl, (C₅-C₈)-cycloalkenyloxy,     (C₅-C₈)-cycloalkynyl, (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkyl,     (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkoxy, phenyl, phenyl-(C₁-C₈)-alkyl,     phenyl-(C₁-C₈)-alkoxy, phenoxy, phenoxy-(C₁-C₈)-alkyl,     phenoxy-(C₁-C₈)-alkoxy, phenylamino, phenylamino-(C₁-C₈)-alkyl,     phenylamino-(C₁-C₈)-alkoxy or a 5- or 6-membered monocyclic or 9- or     10-membered bicyclic heterocycle which is optionally attached via an     alkylene group or an alkoxy group and contains 1, 2, 3 or 4     heteroatoms selected from the group consisting of O, N and S, where     each of the 20 last-mentioned radicals is optionally substituted in     the cyclic moiety by one or more identical or different radicals     R^(cc), and -   R^(bb) and R^(cc) independently of one another each represent     halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy or     (C₁-C₄)-haloalkoxy or in the case of saturated or partially     unsaturated cyclic base groups also represent oxo and -   M represents an equivalent of a cation, -    preferably a metal ion equivalent, an ammonium ion which is     optionally substituted by 1 to 4 identical or different radicals     from the group consisting of (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,     (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₅-C₆)-cycloalkenyl,     (C₅-C₆)-cycloalkynyl, phenyl, (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl,     (C₅-C₆)-cycloalkenyl-(C₁-C₄)-alkyl, phenyl-(C₁-C₄)-alkyl, or a     tertiary sulphonium ion which is preferably substituted by 3     identical or different radicals from the group consisting of     (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,     (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkynyl, phenyl,     (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl,     (C₅-C₆)-cycloalkenyl-(C₁-C₄)-alkyl, phenyl-(C₁-C₄)-alkyl, in     particular (C₁-C₄)-alkyl, -   m represents 0, 1, 2 or 3, preferably 0, 1 or 2, in particular 0 or     1, and -   n represents 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2 or 3.

In the formula (I), the formula “(R¹)_(m)” means m radicals R¹ which are attached as substituents at the pyridyl ring in question, where the radicals in the case of m greater than 1 may be identical or different and have the meaning mentioned in each case in more detail. In the case m=0, the pyridyl ring in question is not substituted by substituents R¹, i.e. all ring carbon atoms of the pyridyl ring in positions 2, 4 and 6 of the pyridin-3-yl radical are attached to a hydrogen atom.

In the formula (I), the formula “(R²)_(n)” means n radicals R² which are attached as substituents at the phenyl ring in question, where the radicals in the case of n greater than 1 may be identical or different and have the meaning mentioned in each case in more detail. In the case n=0, the phenyl ring in question is not substituted by substituents R², i.e. all ring carbon atoms of the phenyl ring in positions 2 to 6 of the phenyl radical are attached to a hydrogen atom.

The compounds of the formula (I) according to the invention include all stereoisomers which can occur on the basis of the centres of asymmetry or double bonds in the molecule whose configuration is not designated specifically in the formula or which are not specified explicitly, and mixtures thereof, including the racemic compounds and the mixtures enriched partly with particular stereoisomers. The invention also includes all tautomers, such as keto and enol tautomers, and their mixtures and salts, if appropriate functional groups are present.

In positions 3 and 4 of the substituted butanoic acid skeleton, the compounds of the formula (I) contain two centres of chirality, and they therefore occur as at least four stereoisomers and mixtures thereof, i.e. 2 enantiomeric erythro isomers and 2 enantiomeric threo isomers. Depending on the substituents (R¹)_(m) and (R²)_(n) R³ and R⁴, one or more further centres of chirality may be present.

Accordingly, the invention also provides erythro/threo mixtures (diastereomer mixtures) of the compounds of the formula (I).

The invention also provides the racemic erythro isomers or the racemic threo isomers of the compounds of the formula (I).

The invention also provides the optically active (3R,4S) and (3S,4R) erythro isomers and mixtures thereof having an excess of one enantiomer.

The invention also provides the optically active (3R,4R) and (3S,4S) threo isomers and mixtures thereof having an excess of one enantiomer.

Owing to the two centres of chirality in positions 3 and 4, compounds of the same chemical constitution exist as 4 stereoisomeric configurations, namely two erythro enantiomers having the configurations (3S,4R) [=erythro-1] and (3R,4S) [=erythro-2], respectively, and two threo enantiomers having the configurations (3S,4S) [=threo-1] and (3R,4R) [=threo-2], respectively; see the scheme below:

The compounds (I) according to the invention represent diastereomer mixtures of the 4 stereoisomers, but also embrace the separated diastereomeric erythro or threo forms, in each case as a racemic mixture of the erythro enantiomers or threo enantiomers or as pure or stereochemically enriched enantiomers erythro-1, erythro-2, threo-1 or threo-2 mentioned above.

Preference is given to the diastereomer mixtures of the formula (I) (erythro/threo mixtures).

Preference is also given to the racemic erythro mixtures of the formula (I) of the aforementioned enantiomers erythro-1 and erythro-2 in a ratio of 50:50.

Preference is furthermore given to the racemic threo mixtures of the formula (I) of the aforementioned enantiomers threo-1 and threo-2 in a ratio of 50:50.

More preference is given to the (3R,4R) enantiomers threo-2 of the formula (Ia) or salts thereof

in which (R¹)_(m) and (R²)_(n) are as defined in formula (I), where the stereochemical configuration at the carbon atom in position 3 of the butanoic acid derivative has a stereochemical purity of 60 to 100% (R), preferably 70 to 100% (R), more preferably 80 to 100% (R), in particular 90 to 100% (R), based on the mixture of threo enantiomers present, and the stereochemical configuration at the carbon atom in position 4 of the butanoic acid derivative has a stereochemical purity of 60 to 100% (R), preferably 70 to 100% (R), more preferably 80 to 100% (R), in particular 90 to 100% (R), based on the mixture of threo enantiomers present.

In the case of R⁴═H or in the case of suitable acidic substituents, the compounds of the formula (I) are able to form salts by reaction with bases where the acidic hydrogen is replaced by an agriculturally suitable cation.

By addition of a suitable inorganic or organic acid onto a basic group, such as, for example, amino or alkylamino or else the nitrogen atom in the pyridyl ring, the compounds of the formula (I) are able to form salts. Suitable acidic groups present, such as, for example, carboxylic acid groups, are able to form inner salts with groups which for their part can be protonated, such as amino groups.

The compounds of the formula (I) may preferably be present in the form of agriculturally usable salts, where the type of salt is generally otherwise immaterial. In general, suitable salts are the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the herbicidal activity of the compounds (I).

Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium or potassium, of the alkaline earth metals, preferably calcium or magnesium, and of the transition metals, preferably manganese, copper, zinc or iron. The cation used may also be ammonium or substituted ammonium, where one to four hydrogen atoms may be replaced here by (C₁-C₄)-alkyl, hydroxy-(C₁-C₄)-alkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, hydroxy-(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium. Also suitable are phosphonium ions, sulphonium ions, preferably tri(C₁-C₄)sulphonium, in particular trimethylsulphonium, or sulphoxonium ions, preferably tri(C₁-C₄)sulphoxonium, in particular trimethylsulphoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulphate, sulphate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of (C₁-C₄)-alkanoic acids, preferably formate, acetate, propionate, butyrate or trifluoroacetate.

In formula (I) and in all subsequent formulae, chemical radicals are referred to by names which are collective terms for the enumeration of individual group members or specifically refer to individual chemical radicals. In general, terms are used which are familiar to the person skilled in the art and/or in particular have the meanings illustrated below.

A hydrolyzable radical (see definition of R⁴) is a radical which can be hydrolyzed under application conditions, for example a radical which can be hydrolyzed even in the spray liquor or in particular under the physiological conditions in plants, where a compound of the formula (I) having the carboxylic ester group —CO—OR⁴ (R⁴ is not hydrogen) is hydrolyzed to the compound of the formula (I) having the carboxylic acid group —CO—OH (i.e. the compound (I) where R⁴═H). Expressly, the definition of the hydrolyzable radicals also includes radicals where R⁴=hydrocarbon radical or heterocyclyl radical, the two last-mentioned radicals being unsubstituted or substituted, even if some of them are hydrolyzable comparatively slowly.

A hydrocarbon radical is an aliphatic, cycloaliphatic or aromatic monocyclic or, in the case of an optionally substituted hydrocarbon radical, also a bicyclic or polycyclic organic radical based on the elements carbon and hydrogen, including, for example, the radicals alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, phenyl, naphthyl, indanyl, indenyl, etc.; this applies correspondingly to hydrocarbon radicals in composite meanings, such as hydrocarbonoxy radicals or other hydrocarbon radicals attached via heteroatom groups.

Unless defined in more detail, the hydrocarbon radicals preferably have 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, in particular 1 to 12 carbon atoms. The hydrocarbon radicals, also in the special radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio, and also the corresponding unsaturated and/or substituted radicals may in each case be straight-chain or branched in the carbon skeleton.

The expression “(C₁-C₄)-alkyl” is a brief notation for alkyl having from 1 to 4 carbon atoms, i.e. encompasses the methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radicals. General alkyl radicals with a larger specified range of carbon atoms, e.g. “(C₁-C₆)-alkyl”, correspondingly also encompass straight-chain or branched alkyl radicals with a greater number of carbon atoms, i.e. according to the example also the alkyl radicals having 5 and 6 carbon atoms.

Unless stated specifically, preference is given to the lower carbon skeletons, for example having from 1 to 6 carbon atoms, or having from 2 to 6 carbon atoms in the case of unsaturated groups, in the case of the hydrocarbyl radicals such as alkyl, alkenyl and alkynyl radicals, including in composite radicals. Alkyl radicals, including in the combined definitions such as alkoxy, haloalkyl, etc., are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl radicals are defined as the possible unsaturated radicals corresponding to the alkyl radicals; alkenyl is, for example, vinyl, allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl, 2-methylpentenyl or hexenyl group, preferably allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl or 1-methylbut-2-en-1-yl.

Alkenyl also includes in particular straight-chain or branched hydrocarbon radicals having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulated double bonds, for example allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.

Alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. Alkynyl also includes, in particular, straight-chain or branched hydrocarbon radicals having more than one triple bond or else having one or more triple bonds and one or more double bonds, for example 1,3-butatrienyl or 3-penten-1-yn-1-yl.

A 3- to 9-membered carbocyclic ring is (C₃-C₉)-cycloalkyl or (C₅-C₉)-cycloalkenyl. (C₃-C₉)-Cycloalkyl is a carbocyclic saturated ring system having preferably 3-9 carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl or cyclononyl. In the case of substituted cycloalkyl, cyclic systems with substituents are included, where the substituents may also be bonded by a double bond on the cycloalkyl radical, for example an alkylidene group such as methylidene. (C₅-C₉)-Cycloalkenyl is a carbocyclic, nonaromatic, partially unsaturated ring system having 5-9 carbon atoms, for example 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl. In the case of substituted cycloalkenyl, the explanations for substituted cycloalkyl apply correspondingly.

Alkylidene, for example also in the form of (C₁-C₁₀)-alkylidene, is the radical of a straight-chain or branched alkane which is bonded via a double bond, the position of the binding site not being fixed. In the case of a branched alkane, the only positions possible are, of course, those in which two hydrogen atoms can be replaced by the double bond; radicals are, for example, ═CH₂, ═CH—CH₃, ═C(CH₃)—CH₃, ═C(CH₃)—C₂H₅ or ═C(C₂H₅)—C₂H₅.

Halogen is, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, -alkenyl and -alkynyl are alkyl, alkenyl and alkynyl, respectively, which are partially or fully substituted by identical or different halogen atoms, preferably from the group consisting of fluorine, chlorine, bromine and iodine, in particular from the group consisting of fluorine, chlorine and bromine, very particularly from the group consisting of fluorine and chlorine, for example monohaloalkyl, perhaloalkyl, CF₃, CHF₂, CH₂F, CF₃CF₂, CH₂FCHCl, CCl₃, CHCl₂, CH₂CH₂Cl; haloalkoxy is, for example, OCF₃, OCHF₂, OCH₂F, CF₃CF₂O, OCH₂CF₃ and OCH₂CH₂Cl; this applies correspondingly to haloalkenyl and other halogen-substituted radicals such as, for example, halocycloalkyl.

Aryl is a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl.

Optionally substituted aryl also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, where the point of attachment is at the aromatic system.

A heterocyclic radical (heterocyclyl) comprises at least one heterocyclic ring (=carbocyclic ring in which at least one carbon atom is replaced by a heteroatom, preferably by a heteroatom from the group consisting of N, O, S, P, B, Si, Se), which is saturated, unsaturated or heteroaromatic and may be unsubstituted or substituted, where the point of attachment is located at a ring atom.

Unless defined otherwise it preferably contains one or more, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably from the group consisting of N, O, and S; it is preferably an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms. The heterocyclic radical may, for example, be a heteroaromatic radical or ring (heteroaryl), such as, for example, a monocyclic, bicyclic or polycyclic aromatic system in which at least 1 ring contains one or more heteroatoms.

If the heterocyclyl radical or the heterocyclic ring is optionally substituted, it can be fused to other carbocyclic or heterocyclic rings. Preference is given to benzo-fused heterocyclic or heteroaromatic rings.

Optionally substituted heterocyclyl also includes polycyclic systems, such as, for example, 8-aza-bicyclo[3.2.1]octanyl or 1-aza-bicyclo[2.2.1]heptyl.

Optionally substituted heterocyclyl also includes spirocyclic systems, such as, for example, 1-oxa-5-aza-spiro[2.3]hexyl.

It is preferably a radical of a heteroaromatic ring having a heteroatom from the group consisting of N, O and S, for example the radical of a five- or six-membered ring, such as pyridyl, pyrrolyl, thienyl or furyl;

it is furthermore preferably a radical of a corresponding heteroaromatic ring having 2, 3 or 4 heteroatoms, for example pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, tetrazinyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl or triazolyl or tetrazolyl. Here, preference is given to a radical of a heteroaromatic five- or six-membered ring having 1 to 4 heteroatoms, such as, for example, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, tetrazolyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, 1,2,4,5-tetrazinyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl.

More preference is given here to heteroaromatic radicals of five-membered heterocycles having 3 nitrogen atoms, such as 1,2,3-triazol-1-yl, 1,2,3-triazol-4-yl, 1,2,3-triazol-5-yl, 1,2,5-triazol-1-yl, 1,2,5-triazol-3-yl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl;

more preference is also given here to heteroaromatic radicals of six-membered heterocycles having 3 nitrogen atoms, such as 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl, 1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl; more preference is also given here to heteroaromatic radicals of five-membered heterocycles having two nitrogen atoms and one oxygen atom, such as 1,2,4-oxadiazol-3-yl; 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl, more preference is also given here to heteroaromatic radicals of five-membered heterocycles having two nitrogen atoms and one sulphur atom, such as 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,5-thiadiazol-3-yl; more preference is also given here to heteroaromatic radicals of five-membered heterocycles having four nitrogen atoms, such as 1,2,3,4-tetrazol-1-yl, 1,2,3,4-tetrazol-5-yl, 1,2,3,5-tetrazol-1-yl, 1,2,3,5-tetrazol-4-yl, 2H-1,2,3,4-tetrazol-5-yl, 1H-1,2,3,4-tetrazol-5-yl, more preference is also given here to heteroaromatic radicals of six-membered heterocycles such as 1,2,4,5-tetrazin-3-yl; more preference is also given here to heteroaromatic radicals of five-membered heterocycles having three nitrogen atoms and one oxygen or sulphur atom, such as 1,2,3,4-oxatriazol-5-yl; 1,2,3,5-oxatriazol-4-yl; 1,2,3,4-thiatriazol-5-yl; 1,2,3,5-thiatriazol-4-yl; more preference is also given here to heteroaromatic radicals of six-membered heterocycles such as, for example, 1,2,4,6-thiatriazin-1-yl; 1,2,4,6-thiatriazin-3-yl; 1,2,4,6-thiatriazin-5-yl.

Furthermore preferably, the heterocyclic radical or ring is a partially or fully hydrogenated heterocyclic radical having one heteroatom from the group consisting of N, O and S, for example oxiranyl, oxetanyl, oxolanyl (=tetrahydrofuryl), oxanyl, pyrrolinyl, pyrrolidyl or piperidyl.

It is also preferably a partially or fully hydrogenated heterocyclic radical having 2 heteroatoms from the group consisting of N, O and S, for example piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl and morpholinyl. Suitable substituents for a substituted heterocyclic radical are the substituents specified later on below, and additionally also oxo. The oxo group may also occur on the hetero-ring atoms which are able to exist in different oxidation states, as in the case of N and S, for example.

Preferred examples of heterocyclyl are a heterocyclic radical having from 3 to 6 ring atoms from the group consisting of pyridyl, thienyl, furyl, pyrrolyl, oxiranyl, 2-oxetanyl, 3-oxetanyl, oxolanyl (=tetrahydrofuryl), pyrrolidyl, piperidyl, especially oxiranyl, 2-oxetanyl, 3-oxetanyl or oxolanyl, or is a heterocyclic radical having two or three heteroatoms, for example pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl or morpholinyl.

Preferred heterocyclic radicals are also benzo-fused heteroaromatic rings, for example benzofuryl, benzisofuryl, benzothiophenyl, benzisothiophenyl, isobenzothiophenyl, indolyl, isoindolyl, indazolyl, benzimidazolyl, benzotriazolyl, benzoxazolyl, 1,2-benzisoxazolyl, 2,1-benzisoxazolyl, benzothiazolyl, 1,2-benzisothiazolyl, 2,1-benzisothiazolyl, 1,2,3-benzoxadiazolyl, 2,1,3-benzoxadiazolyl, 1,2,3-benzothiadiazolyl, 2,1,3-benzothiadiazolyl, quinolyl (quinolinyl), isoquinolyl (isoquinolinyl), quinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl, pteridinyl, indolizinyl, benzo-1,3-dioxylyl, 4H-benzo-1,3-dioxinyl and 4H-benzo-1,4-dioxinyl, and, where possible, N-oxides and salts thereof.

When a base structure is substituted “by one or more radicals” from a list of radicals (=group) or a generically defined group of radicals, this in each case includes simultaneous substitution by a plurality of identical and/or structurally different radicals. Substituted radicals, such as a substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl radical, are, for example, a substituted radical derived from the unsubstituted base structure, where the substituents are, for example, one or more, preferably 1, 2 or 3, radicals from the group consisting of halogen, alkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino such as acylamino, mono- and dialkylamino, and alkylsulphinyl, alkylsulphonyl and, in the case of cyclic radicals, also alkyl, haloalkyl, alkylthioalkyl, alkoxyalkyl, optionally substituted mono- and dialkylaminoalkyl and hydroxyalkyl; in the term “substituted radicals”, such as substituted alkyl, etc., substituents include, in addition to the saturated hydrocarbon radicals mentioned, corresponding unsaturated aliphatic and aromatic radicals, such as optionally substituted alkenyl, alkynyl, alkenyloxy, alkynyloxy, phenyl and phenoxy. In the case of substituted cyclic radicals having aliphatic moieties in the ring, cyclic systems with those substituents which are bonded on the ring by a double bond are also included, for example substituted by an alkylidene group such as methylidene or ethylidene.

The term “radicals from the group consisting of (followed by the group=list of the substituents)” is, wherever used, meant to be synonymous with “radicals selected from the group consisting of ( . . . )”. The term “one or more radicals from the group consisting of (followed by the group=list of the substituents)” is, wherever used, meant to be synonymous with “one or more identical or different radicals selected from the group consisting of ( . . . )”.

The substituents given by way of example (“first substituent level”) can, if they include hydrocarbon-containing fractions, be further substituted therein if desired (“second substituent level”), by for example one of the substituents as defined for the first substituent level. Corresponding further substituent levels are possible. The term “substituted radical” preferably embraces just one or two substituent levels.

“Parent radical” refers to the respective base structure of a radical to which substituents of a substituent level are attached.

Preferred substituents for the substituent levels are, for example, amino, hydroxyl, halogen, nitro, cyano, mercapto, carboxyl, carbonamide, SF₅, aminosulphonyl, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, monoalkylamino, dialkylamino, N-alkanoylamino, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkenyloxy, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, alkanoyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkylthio, cycloalkylthio, alkenylthio, cycloalkenylthio, alkynylthio, alkylsulphinyl, alkylsulphonyl, monoalkylaminosulphonyl, dialkylaminosulphonyl, N-alkylaminocarbonyl, N,N-dialkylaminocarbonyl, N-alkanoylaminocarbonyl, N-alkanoyl-N-alkylaminocarbonyl, aryl, aryloxy, benzyl, benzyloxy, benzylthio, arylthio, arylamino and benzylamino.

Two substituents together may also form a saturated or unsaturated hydrocarbon bridge or a corresponding bridge in which carbon atoms, CH groups or CH₂ groups are replaced by heteroatoms, thus forming a fused-on or fused cycle. Here, with preference benzo-fused systems based on the base structure are formed.

Optionally substituted phenyl is preferably phenyl or phenyl which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio and nitro, in particular phenyl which is optionally substituted by one or more radicals from the group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and (C₁-C₄)-alkoxy.

In the case of radicals having carbon atoms, preference is given to those having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, especially 1 or 2 carbon atoms. Preference is generally given to substituents from the group consisting of halogen, e.g. fluorine and chlorine, (C₁-C₄)-alkyl, preferably methyl or ethyl, (C₁-C₄)-haloalkyl, preferably trifluoromethyl, (C₁-C₄)-alkoxy, preferably methoxy or ethoxy, (C₁-C₄)-haloalkoxy, nitro and cyano. Particular preference is given here to the substituents methyl, methoxy, fluorine and chlorine.

Substituted amino, such as mono- or disubstituted amino, is a radical from the group consisting of the substituted amino radicals which are N-substituted, for example, by one or two identical or different radicals from the group consisting of alkyl, alkoxy, acyl and aryl; preferably mono- and dialkylamino, mono- and diarylamino, acylamino, N-alkyl-N-arylamino, N-alkyl-N-acylamino and N-heterocycles; preference is given to alkyl radicals having from 1 to 4 carbon atoms; aryl is preferably phenyl or substituted phenyl; acyl is as defined below, preferably (C₁-C₄)-alkanoyl. The same applies to substituted hydroxylamino or hydrazino.

Acyl is a radical of an organic acid which arises in a formal sense by removal of a hydroxyl group on the acid function, and the organic radical in the acid may also be bonded to the acid function via a heteroatom. Examples of acyl are the —CO—R radical of a carboxylic acid HO—CO—R and radicals of acids derived therefrom, such as those of thiocarboxylic acid, optionally N-substituted iminocarboxylic acids or the radical of carbonic monoesters, N-substituted carbamic acid, sulphonic acids, sulphinic acids, N-substituted sulphonamide acids, phosphonic acids or phosphinic acids.

Acyl is, for example, formyl, alkylcarbonyl such as [(C₁-C₄)-alkyl]carbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulphonyl, alkylsulphinyl, N-alkyl-1-iminoalkyl and other radicals of organic acids. The radicals may each be substituted further in the alkyl or phenyl moiety, for example in the alkyl moiety by one or more radicals from the group consisting of halogen, alkoxy, phenyl and phenoxy; examples of substituents in the phenyl moiety are the substituents already mentioned above in general for substituted phenyl.

Acyl is preferably an acyl radical in the narrower sense, i.e. a radical of an organic acid in which the acid group is bonded directly to the carbon atom of an organic radical, for example formyl, alkylcarbonyl such as acetyl or [(C₁-C₄)-alkyl]carbonyl, phenylcarbonyl, alkylsulphonyl, alkylsulphinyl and other radicals of organic acids.

More preferably, acyl is an alkanoyl radical having 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms. Here, (C₁-C₄)-alkanoyl is the radical of an alkanoic acid having 1 to 4 carbon atoms formed after removal of the OH group of the acid group, i.e. formyl, acetyl, n-propionyl, isopropionyl or n-, i-, sec- or tert-butanoyl.

The “yl position” of a radical denotes the carbon atom having the free bond.

Compounds of the formula (I) according to the invention and compounds of the formula (I) used according to the invention and/or salts thereof are in short also referred to as “compounds (I)”.

The invention also provides all stereoisomers which are encompassed by formula (I) and mixtures thereof. Such compounds of the formula (I) contain one or more asymmetric carbon atoms or else double bonds which are not stated separately in the general formulae (I). The possible stereoisomers defined by their specific three-dimensional shape, such as enantiomers, diastereomers, Z- and E-isomers, are all encompassed by the formula (I) and can be obtained from mixtures of the stereoisomers by customary methods or else prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials.

The invention also provides all tautomers of the compounds of the formula (I) which may result from a hydrogen atom shift (for example keto-enol tautomers). The compound of the formula (I) also includes the tautomers, even if formally the formula (I) correctly describes only one of the respective tautomers which are in equilibrium with one another or which can be converted into one another.

The compounds of the formula (I) also include all physical forms in which they may be present as a pure substance or, if appropriate, as a mixture with other compounds, in particular also polymorphic crystal forms of the compounds of the formula (I) or salts thereof or solvent adducts (for example hydrates).

Primarily for reasons of higher herbicidal activity, better selectivity, better producibility, better formulatability and/or other relevant properties, compounds of the abovementioned formula (I) according to the invention or their salts or their use according to the invention are of particular interest in which individual radicals have one of the preferred meanings already specified or specified below, or in particular those in which one or more of the preferred meanings already specified or specified below occur in combination.

Compounds of the formula (I) according to the invention and their uses according to the invention with the preferred meanings listed below of the symbols or chemical radicals or chemical groups in question are of particular interest, irrespective of the respective other radicals according to the symbols (R¹)_(m), (R²)_(n), R³, R⁴ and the definitions of m and n in formula (I) and the definitions of the radicals (or chemical groups) according to the symbols R⁵ to R¹⁹, Het¹ to Het⁷, M, R* and R**, R^(A), R^(B), R^(aa), R^(bb) and R^(cc) in the corresponding sub-meanings of radicals in the formula (I).

Preference is given to compounds (I) in which

-   (R¹)_(m) represents m substituents R¹, -    where R¹, if m=1, or each of the substituents R¹, if m is greater     than 1, independently of the others represents halogen, cyano,     nitro, hydroxy, (C₁-C₆)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl,     (C₁-C₆)-alkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulphinyl,     (C₁-C₆)-alkylsulphonyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,     (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulphinyl,     (C₁-C₄)-haloalkylsulphonyl, (C₂-C₄)-haloalkenyl,     (C₂-C₄)-haloalkynyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,     (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl which is     optionally substituted by one or more radicals from the group     consisting of halogen and (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkoxy which     is optionally substituted by one or more radicals from the group     consisting of halogen and (C₁-C₄)-alkyl, or a radical of the formula     C(O)OR⁵, C(O)NR⁶R⁷, C(O)-Het¹, NR⁸R⁹ or Het² -    or where in each case two groups R¹ located ortho at the ring or R¹     and R³ together represent a group of the formula —Z¹-A*-Z² in which     -   A* represents an alkylene group having 1 to 4 carbon atoms which         is optionally substituted by one or more radicals from the group         consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,         (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy,     -   Z¹ represents a direct bond, O or S and     -   Z² represents a direct bond, O or S, -    where the group —Z¹-A*-Z² together with the carbon atoms, attached     to the group, of the phenyl ring form a fused-on 5- or 6-membered     ring, -   R⁵ represents hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,     (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₂-C₄)-alkenyl,     (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl or the group M mentioned,     preferably hydrogen, (C₁-C₄)-alkyl or the group M mentioned, -   R⁶, R⁷, R⁸, R⁹, Het¹ and Het² have the meanings mentioned,     preferably -   R⁶, R⁷, R⁸ and R⁹ independently of one another each represent     hydrogen or (C₁-C₄)-alkyl which is unsubstituted or substituted by     one or more radicals from the group consisting of halogen, nitro,     cyano and phenyl, or (C₃-C₆)-cycloalkyl or phenyl, where each of the     2 last-mentioned radicals in each case independently of the other is     unsubstituted or substituted by one or more radicals from the group     consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, phenyl and     benzyl, in particular hydrogen, (C₁-C₄)-alkyl or (C₁-C₄)-haloalkyl, -   Het¹ and Het² independently of one another each represent a     saturated or partially unsaturated radical of a heterocycle having 3     to 6 ring atoms and at least one nitrogen atom as ring heteroatoms     at position 1 of the ring and optionally 1, 2 or 3 further ring     heteroatoms from the group consisting of N, O and S, where the     radical of the heterocycle is attached at the nitrogen atom in     position 1 of the ring to the remainder of the molecule of the     compound of the formula (I) and where the heterocycle is     unsubstituted or substituted by one or more radicals from the group     consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo,     preferably the radical of a saturated heterocycle of the type     mentioned, in particular a morpholino, piperidino or pyrrolidino     group, and -   m represents 0, 1, 2 or 3, preferably 0, 1 or 2, in particular 0 or     1.

More preference is given to compounds (I) in which

-   (R¹)_(m) represents m substituents R¹, -    where R¹, if m=1, or each of the substituents R¹, if m is greater     than 1, independently of the others represents halogen, cyano,     nitro, hydroxy, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio,     (C₁-C₄)-alkylsulphinyl, (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-haloalkyl,     (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkylthio,     (C₁-C₄)-haloalkylsulphinyl, (C₁-C₄)-haloalkylsulphonyl,     (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl, or a radical of     the formula C(O)OR⁵, C(O)NR⁶R⁷, C(O)-Het¹, NR⁸R⁹ or Het², -    or where in each case two groups R¹ located ortho at the ring or R¹     and R³ together represent a group of the formula —Z¹-A*-Z² in which     -   A* represents an alkylene group having 1 to 4 carbon atoms which         is optionally substituted by one or more radicals from the group         consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,         (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy,     -   Z¹ represents a direct bond, O or S and     -   Z² represents a direct bond, O or S, -    where the group —Z¹-A*-Z² together with the carbon atoms, attached     to the group, of the phenyl ring form a fused-on 5- or 6-membered     ring, -   R⁵ represents hydrogen, (C₁-C₄)-alkyl or the group M mentioned, -   R⁶, R⁷, R⁸ and R⁹ independently of one another each represent     hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, benzyl,     (C₃-C₆)-cycloalkyl or phenyl, in particular hydrogen, methyl or     ethyl, -   Het¹ and Het² independently of one another each represent a     morpholino, piperidino or pyrrolidino group and -   m represents 0, 1, 2 or 3, preferably 0, 1 or 2, in particular 0 or     1.

Here, more preference is given to compounds (I) in which

-   (R¹)_(m) represents m substituents R¹, -   where R¹, if m=1, or each of the substituents R¹, if m is greater     than 1, independently of the others represents halogen, cyano,     nitro, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio,     (C₁-C₂)-alkylsulphinyl, (C₁-C₂)-alkylsulphonyl, (C₁-C₂)-haloalkyl,     (C₁-C₂)-haloalkoxy, (C₁-C₂)-haloalkylthio,     (C₁-C₂)-haloalkylsulphinyl, (C₁-C₂)-haloalkylsulphonyl or     (C₁-C₂)-alkoxy-(C₁-C₂)-alkyl, -    in particular each of the substituents R¹ independently of the     others represents halogen, such as fluorine, chlorine, bromine or     iodine, or cyano, nitro, methyl, methoxy, methylthio,     methylsulphinyl, methylsulphonyl, trifluoromethyl, trifluoromethoxy,     difluoromethoxy, trifluoroalkylthio, trifluoromethylsulphinyl or     trifluoromethylsulphonyl, in particular cyano or halogen such as     fluorine, chlorine or bromine, and -   m represents 0, 1, 2 or 3, preferably 0, 1 or 2, in particular 0 or     1.

More preference is given to compounds of the formula (I) or salts thereof in which

-   m is 0 (=the number zero, i.e. no substituents R¹ are present, i.e.     all respective free bonds at the ring are occupied by hydrogen) or     preferably -   (R¹)_(m) represents 2-bromo, 4-bromo, 6-bromo, 2-chloro, 4-chloro,     6-chloro, 2-fluoro, 4-fluoro, 6-fluoro, 2-cyano, 4-cyano, 6-cyano,     2-methyl, 4-methyl, 6-methyl, 2-ethyl, 4-ethyl, 6-ethyl, 2-CF₃,     4-CF₃, 6-CF₃, 2-methoxy, 4-methoxy, 6-methoxy, 2-ethoxy, 4-ethoxy,     6-ethoxy, 2-trifluoromethoxy, 4-trifluoromethoxy,     6-trifluoromethoxy, 2-difluoromethoxy, 4-difluoromethoxy,     6-difluoromethoxy, 2-methylthio, 4-methylthio, 6-methylthio,     2-methylsulphinyl, 4-methylsulphinyl, 6-methylsulphonyl,     2-methylsulphonyl, 4-methylsulphonyl, 6-methylsulphonyl, 2-nitro,     4-nitro, 6-nitro, 2,4-dimethyl, 2,6-dimethyl, 4,6-dimethyl,     2,4-difluoro, 2,6-difluoro, 4,6-difluoro, 2,4-dichloro,     2,6-dichloro, 4,6-dichloro, (2-Cl-4-F), (2-Cl-6-F), (4-Cl-6-F),     (2-F-4-Cl), (2-F-6-Cl), (4-F-6-Cl), 2,4,6-trifluoro or     2,4,6-trichloro, where the numbering of the radical refers to the     position of the radical at the pyridin-3-yl radical in which the     nitrogen atom is located in position 1 and the carbon atom attached     to the butyric acid parent structure is located in position 3 in the     ring.

Preference is also given to compounds (I) in which

-   (R²)_(n) represents n substituents R², -    where R², if n=1, or each of the substituents R², if n is greater     than 1, independently of the others represents halogen, cyano,     nitro, hydroxy, (C₁-C₆)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl,     (C₁-C₆)-alkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulphinyl,     (C₁-C₆)-alkylsulphonyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,     (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulphinyl,     (C₁-C₄)-haloalkylsulphonyl, (C₂-C₄)-haloalkenyl,     (C₂-C₄)-haloalkynyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,     (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl which is     optionally substituted by one or more radicals from the group     consisting of halogen and (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkoxy which     is optionally substituted by one or more radicals from the group     consisting of halogen and (C₁-C₄)-alkyl, or a radical of the formula     C(O)OR¹⁰, C(O)NR¹¹R¹², C(O)-Het³, NR¹³R¹⁴ or Het⁴ -    or where in each case two groups R² located ortho at the ring     together are a group of the formula —Z³-A**-Z⁴ in which     -   A** represents an alkylene group having 1 to 4 carbon atoms         which is optionally substituted by one or more radicals from the         group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,         (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy,     -   Z³ represents a direct bond, O or S and     -   Z⁴ represents a direct bond, O or S, -    where the group —Z³-A**-Z⁴ together with the carbon atoms, attached     to the group, of the phenyl ring form a fused-on 5- or 6-membered     ring, -   R¹⁰ represents hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,     (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₂-C₄)-alkenyl,     (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl or the group M mentioned, -   R¹¹, R¹², R¹³, R¹⁴, Het³ and Het⁴ have the meanings mentioned,     preferably -   R¹¹, R¹², R¹³ and R¹⁴ independently of one another each represent     hydrogen or (C₁-C₄)-alkyl which is unsubstituted or substituted by     one or more radicals from the group consisting of halogen, nitro,     cyano and phenyl, or (C₃-C₆)-cycloalkyl or phenyl, where each of the     2 last-mentioned radicals in each case independently of the other is     unsubstituted or substituted by one or more radicals from the group     consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, phenyl and     benzyl, -   Het³ and Het⁴ independently of one another each represent a     saturated or partially unsaturated radical of a heterocycle having 3     to 6 ring atoms and at least one nitrogen atom as ring heteroatoms     at position 1 of the ring and optionally 1, 2 or 3 further ring     heteroatoms from the group consisting of N, O and S, where the     radical of the heterocycle is attached at the nitrogen atom in     position 1 of the ring to the remainder of the molecule of the     compound of the formula (I) and where the heterocycle is     unsubstituted or substituted by one or more radicals from the group     consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo,     preferably the radical of a saturated heterocycle of the type     mentioned, in particular a morpholino, piperidino or pyrrolidino     group, and -   n represents 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2 or 3.

Here, more preference is given to compounds (I) in which

-   (R²)_(n) represents n substituents R², -    where R², if n=1, or each of the substituents R², if n is greater     than 1, independently of one another represent halogen, cyano,     nitro, hydroxy, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio,     (C₁-C₄)-alkylsulphinyl, (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-haloalkyl,     (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkylthio,     (C₁-C₄)-haloalkylsulphinyl, (C₁-C₄)-haloalkylsulphonyl,     (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl, or a radical of     the formula C(O)OR¹⁰, C(O)NR¹¹R¹², C(O)-Het³, NR¹³R¹⁴ or Het⁴ -    or where in each case two groups R² located ortho at the ring     together are a group of the formula —Z³-A**-Z⁴ in which     -   A** represents an alkylene group having 1 to 4 carbon atoms         which is optionally substituted by one or more radicals from the         group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,         (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy,     -   Z³ represents a direct bond, O or S and     -   Z⁴ represents a direct bond, O or S, -    where the group —Z³-A**-Z⁴ together with the carbon atoms, attached     to the group, of the phenyl ring form a fused-on 5- or 6-membered     ring, -   R¹⁰ represents hydrogen, (C₁-C₄)-alkyl or the group M mentioned, -   R¹¹, R¹², R¹³ and R¹⁴, Het³ and Het⁴ have the meanings mentioned,     preferably R¹¹, R¹², R¹³ and R¹⁴ independently of one another each     represent hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, benzyl,     (C₃-C₆)-cycloalkyl or phenyl, -   Het³ and Het⁴ independently of one another each represent a     morpholino, piperidino or pyrrolidino group and -   n represents 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2, 3 or 4, in     particular 0, 1, 2 or 3.

Here, more preference is given to compounds (I) in which

-   (R²)_(n) represents n substituents R², -   where R², if n=1, or each of the substituents R², if n is greater     than 1, independently of the others represents halogen, cyano,     nitro, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio,     (C₁-C₂)-alkylsulphinyl, (C₁-C₂)-alkylsulphonyl, (C₁-C₂)-haloalkyl,     (C₁-C₂)-haloalkoxy, (C₁-C₂)-haloalkylthio,     (C₁-C₂)-haloalkylsulphinyl, (C₁-C₂)-haloalkylsulphonyl or     (C₁-C₂)-alkoxy-(C₁-C₂)-alkyl, -    in particular each of the substituents R² independently of the     others represents halogen, such as fluorine, chlorine, bromine or     iodine, or cyano, nitro, methyl, methoxy, methylthio,     methylsulphinyl, methylsulphonyl, trifluoromethyl, trifluoromethoxy,     difluoromethoxy, trifluoroalkylthio, trifluoromethylsulphinyl or     trifluoromethylsulphonyl, in particular cyano, nitro or halogen such     as fluorine, chlorine or bromine, and -   n represents 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2, 3 or 4, in     particular 0, 1, 2 or 3.

More preference is given to compounds of the formula (I) or salts thereof in which

-   n represents 0 (=the number zero, i.e. no substituents R² are     present, i.e. all free bonds at the phenyl ring are occupied by     hydrogen) or preferably -   (R²)_(n) represents 2-bromo, 3-bromo, 4-bromo, 2-chloro, 3-chloro,     4-chloro, 2-fluoro, 3-fluoro, 4-fluoro, 2-cyano, 3-cyano, 4-cyano,     2-methyl, 3-methyl, 4-methyl, 2-ethyl, 3-ethyl, 4-ethyl, 2-CF₃,     3-CF₃, 4-CF₃, 2-methoxy, 3-methoxy, 4-methoxy, 2-ethoxy, 3-ethoxy,     4-ethoxy, 2-trifluoromethoxy, 3-trifluoromethoxy,     4-trifluoromethoxy, 2-difluoromethoxy, 3-difluoromethoxy,     4-difluoromethoxy, 2-methylthio, 3-methylthio, 4-methylthio,     2-methylsulphinyl, 3-methylsulphinyl, 4-methylsulphinyl,     2-methylsulphonyl, 3-methylsulphonyl, 4-methylsulphonyl, 2-nitro,     3-nitro, 4-nitro, 2,3-dimethyl, 2,4-dimethyl, 2,5-dimethyl,     2,6-dimethyl, 3,4-dimethyl, 3,5-dimethyl, 2,3-difluoro,     2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro,     3,5-difluoro, 2,3-dichloro, 2,4-dichloro, 2,5-dichloro,     2,6-dichloro, 3,4-dichloro, 3,5-dichloro, (2-Cl-3-F), (2-Cl-4-F),     (2-Cl-5-F), (2-Cl-6-F), (3-Cl-2-F), (3-Cl-4-F), (3-Cl-5-F),     (3-Cl-6-F), (4-Cl-2-F), (4-Cl-3-F), (4-Br-2-F), (4-Br-3-F),     (4-CN-3-F), (4-NO₂-3-F), 2,3,4-trifluoro, 2,3,5-trifluoro,     2,3,6-trifluoro, 2,4,6-trifluoro, 3,4,5-trifluoro, 2,3,4-trichloro,     2,3,5-trichloro, 2,3,6-trichloro, 2,4,6-trichloro, 3,4,5-trichloro     or else (2,6-difluoro-4-Cl), 2,5-dicyano, 2,6-dicyano,     (4-methoxy-3-F), (3-CN-4-F), (3-nitro-4-F), (3-CN-4-Cl),     (3-nitro-4-Cl) or (5-CN-2-F), where the numbering of the radicals     refers to the position of the radical at the phenyl-1-yl radical in     which the carbon atom attached to the 3-position at the butyric acid     parent structure has the 1-position in the ring.

More preference is given to compounds of the formula (I) or salts thereof in which

-   (R²)_(n) represents 2-cyano, 3-cyano, 4-cyano, 2-bromo, 3-bromo,     4-bromo, 2-chloro, 3-chloro, 4-chloro, 2-fluoro, 3-fluoro, 4-fluoro,     2-nitro, 3-nitro, 4-nitro, 2-methoxy, 3-methoxy, 4-methoxy,     2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro,     3,4-difluoro, 3,5-difluoro, 2,3-dichloro, 2,4-dichloro,     2,5-dichloro, 2,6-dichloro, 3,4-dichloro, 3,5-dichloro, (2-Cl-3-F),     (2-Cl-4-F), (2-Cl-5-F), (2-Cl-6-F), (3-Cl-2-F), (3-Cl-4-F),     (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F), (4-Cl-3-F), (4-Br-2-F),     (4-Br-3-F), (4-CN-3-F), (4-NO₂-3-F), 2,3,4-trifluoro,     2,3,5-trifluoro, 2,3,6-trifluoro, 2,4,6-trifluoro, 3,4,5-trifluoro,     2,3,4-trichloro, 2,3,5-trichloro, 2,3,6-trichloro, 2,4,6-trichloro,     3,4,5-trichloro or else (2,6-difluoro-4-Cl), 2,5-dicyano,     2,6-dicyano, (4-methoxy-3-F), (3-CN-4-F), (3-nitro-4-F),     (3-CN-4-Cl), (3-nitro-4-Cl) or (5-CN-2-F).

More preference is also given to compounds of the formula (I) or salts thereof in which

-   (R²)_(n) represents 3-chloro, 4-chloro, 2-fluoro, 3-fluoro,     4-fluoro, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro,     3,4-difluoro, 3,5-difluoro, 3,4-dichloro, 3,5-dichloro, (3-Cl-2-F),     (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F), (4-Cl-3-F).

Here, particular preference is given to:

Compounds of the formula (I) or salts thereof in which (R²)_(n) represents 3-chloro. Compounds of the formula (I) or salts thereof in which (R²)_(n) represents 4-chloro. Compounds of the formula (I) or salts thereof in which (R²)_(n) represents 2-fluoro. Compounds of the formula (I) or salts thereof in which (R²)_(n) represents 3-fluoro. Compounds of the formula (I) or salts thereof in which (R²)_(n) represents 4-fluoro. Compounds of the formula (I) or salts thereof in which (R²)_(n) represents 2,3-difluoro. Compounds of the formula (I) or salts thereof in which (R²)_(n) represents 2,4-difluoro. Compounds of the formula (I) or salts thereof in which (R²)_(n) represents 2,5-difluoro. Compounds of the formula (I) or salts thereof in which (R²)_(n) represents 2,6-difluoro. Compounds of the formula (I) or salts thereof in which (R²)_(n) represents 3,4-difluoro. Compounds of the formula (I) or salts thereof in which (R²)_(n) represents 3,5-difluoro. Compounds of the formula (I) or salts thereof in which (R²)_(n) represents (3-Cl-2-F). Compounds of the formula (I) or salts thereof in which (R²)_(n) represents (3-Cl-4-F). Compounds of the formula (I) or salts thereof in which (R²)_(n) represents (3-Cl-5-F). Compounds of the formula (I) or salts thereof in which (R²)_(n) represents (3-Cl-6-F). Compounds of the formula (I) or salts thereof in which (R²)_(n) represents (4-Cl-2-F). Compounds of the formula (I) or salts thereof in which (R²)_(n) represents (4-Cl-3-F). Compounds of the formula (I) or salts thereof in which (R²)_(n) represents (2,6-difluoro-4-Cl).

Preference is also given to compounds (I) in which

-   R³ represents halogen, cyano, nitro, hydroxy, (C₁-C₆)-alkyl,     (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, (C₁-C₆)-alkoxy, (C₁-C₆)-alkylthio,     (C₁-C₆)-alkylsulphinyl, (C₁-C₆)-alkylsulphonyl, (C₁-C₄)-haloalkyl,     (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkylthio,     (C₁-C₄)-haloalkylsulphinyl, (C₁-C₄)-haloalkylsulphonyl,     (C₂-C₄)-haloalkenyl, (C₂-C₄)-haloalkynyl,     (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl,     (C₃-C₆)-cycloalkyl which is optionally substituted by one or more     radicals from the group consisting of halogen and (C₁-C₄)-alkyl,     (C₃-C₆)-cycloalkoxy which is optionally substituted by one or more     radicals from the group consisting of halogen and (C₁-C₄)-alkyl, or     a radical of the formula C(O)OR¹⁵, C(O)NR¹⁶R¹⁷, C(O)-Het⁵, NR¹⁸R¹⁹     or Het⁶, -   R¹⁵ represents hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,     (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₂-C₄)-alkenyl,     (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl or the group M mentioned,     preferably hydrogen, (C₁-C₄)-alkyl or the group M mentioned, -   R¹⁶, R¹⁷, R¹⁸, R¹⁹, Het⁵ and Het⁶ have the meanings mentioned,     preferably -   R¹⁶, R¹⁷, R¹⁸ and R¹⁹ independently of one another each represent     hydrogen or (C₁-C₄)-alkyl which is unsubstituted or substituted by     one or more radicals from the group consisting of halogen, nitro,     cyano and phenyl, or (C₃-C₆)-cycloalkyl or phenyl, where each of the     2 last-mentioned radicals in each case independently of the other is     unsubstituted or substituted by one or more radicals from the group     consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, phenyl and     benzyl, in particular hydrogen, (C₁-C₄)-alkyl or (C₁-C₄)-haloalkyl, -   Het⁵ and Het⁶ independently of one another each represent a     saturated or partially unsaturated radical of a heterocycle having 3     to 6 ring atoms and at least one nitrogen atom as ring heteroatoms     at position 1 of the ring and optionally 1, 2 or 3 further ring     heteroatoms from the group consisting of N, O and S, where the     radical of the heterocycle is attached at the nitrogen atom in     position 1 of the ring to the remainder of the molecule of the     compound of the formula (I) and where the heterocycle is     unsubstituted or substituted by one or more radicals from the group     consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo,     preferably the radical of a saturated heterocycle of the type     mentioned, in particular a morpholino, piperidino or pyrrolidino     group.

More preference is given to compounds (I) in which

-   R³ represents halogen, cyano, nitro, hydroxy, (C₁-C₄)-alkyl,     (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl,     (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,     (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulphinyl,     (C₁-C₄)-haloalkylsulphonyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,     (C₃-C₆)-cycloalkyl or a radical of the formula C(O)OR¹⁵,     C(O)NR¹⁶R¹⁷, C(O)-Het⁵, NR¹⁸R¹⁹ or Het⁶, -   R¹⁵ represents hydrogen, (C₁-C₄)-alkyl or the group M mentioned, -   R¹⁶, R¹⁷, R¹⁸ and R¹⁹ independently of one another each represent     hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, benzyl,     (C₃-C₆)-cycloalkyl or phenyl, in particular hydrogen, methyl or     ethyl, -   Het⁵ and Het⁶ independently of one another each represent a     morpholino, piperidino or pyrrolidino group.

Here, more preference is given to compounds (I) in which

-   R³ represents halogen, cyano, nitro, methyl, ethyl, methoxy, ethoxy,     methylthio, ethylthio, (C₁-C₂)-alkylsulphinyl,     (C₁-C₂)-alkylsulphonyl, (C₁-C₂)-haloalkyl, (C₁-C₂)-haloalkoxy,     (C₁-C₂)-haloalkylthio, (C₁-C₂)-haloalkylsulphinyl,     (C₁-C₂)-haloalkylsulphonyl, (C₁-C₂)-alkoxy-(C₁-C₂)-alkyl or     [(C₁-C₄)-alkoxy]carbonyl, R³ represents in particular halogen, such     as fluorine, chlorine, bromine or iodine, or cyano, nitro, methyl,     methoxy, methylthio, methylsulphinyl, methylsulphonyl,     trifluoromethyl, trifluoromethoxy, difluoromethoxy,     trifluoroalkylthio, trifluoromethylsulphinyl,     trifluoromethylsulphonyl, methoxycarbonyl or ethoxycarbonyl, in     particular halogen such as fluorine, chlorine or bromine, and -   m represents 0, 1, 2 or 3, preferably 0, 1 or 2, in particular 0 or     1.

More preference is given to compounds of the formula (I) or salts thereof in which

-   R³ represents bromine, chlorine, fluorine, cyano, methyl, nitro,     methoxycarbonyl or ethoxycarbonyl.

More preference is given to compounds of the formula (I) or salts thereof in which (R¹)_(m) and R³ together represent 5-bromo, 5-chloro, 5-fluoro, 5-cyano, 5-methyl, 5-ethyl, 5-CF₃, 5-methoxy, 5-ethoxy, 5-trifluoromethoxy, 5-difluoromethoxy, 5-methylthio, 5-methylsulphinyl, 5-methylsulphonyl, 5-nitro, 5-methoxycarbonyl, 5-ethoxycarbonyl, 2,5-difluoro, 4,5-difluoro, 5,6-difluoro, 2,5-dichloro, 4,5-dichloro, 5,6-dichloro, 2,5-dibromo, 4,5-dibromo, 5,6-dibromo, 2,5-dimethyl, 4,5-dimethyl, 5,6-dimethyl, 2,5-dicyano, 4,5-dicyano, 5,6-dicyano, (2-Cl-5-F), (4-Cl-5-F), (6-Cl-5-F), (2-Br-5-F), (4-Br-5-F), (6-Br-5-F), (2-F-5-Cl), (4-F-5-Cl), (6-F-5-Cl), (2-F-5-Br), (4-F-5-Br), (6-F-5-Br), (2-Br-5-Cl), (4-Br-5-Cl), (6-Br-5-Cl), (2-Cl-5-Br), (4-Cl-5-Br), (6-Cl-5-Br), (2-CN-5-F), (4-CN-5-F), (6-CN-5-F), (2-CH₃-5-F), (4-CH₃-5-F), (6-CH₃-5-F), (2-OCH₃-5-F), (4-OCH₃-5-F), (6-OCH₃-5-F), (2-OCHF₂-5-F), (4-OCHF₂-5-F), (6-OCHF₂-5-F), (2-CN-5-Cl), (4-CN-5-Cl), (6-CN-5-Cl), (2-CH₃-5-Cl), (4-CH₃-5-Cl), (6-CH₃-5-Cl), (2-OCH₃-5-Cl), (4-OCH₃-5-Cl), (6-OCH₃-5-Cl), (2-OCHF₂-5-Cl), (4-OCHF₂-5-Cl), (6-OCHF₂-5-Cl),

-    (2-CN-5-Br), (4-CN-5-Br), (6-CN-5-Br), (2-CH₃-5-Br), (4-CH₃-5-Br),     (6-CH₃-5-Br), -    (2-OCH₃-5-Br), (4-OCH₃-5-Br), (6-OCH₃-5-Br), (2-OCHF₂-5-Br),     (4-OCHF₂-5-Br), (6-OCHF₂-5-Br), (2-CN-5-CH₃), (4-CN-5-CH₃),     (6-CN-5-CH₃), (2-F-5-CH₃), (4-F-5-CH₃), (6-F-5-CH₃), (2-Cl-5-CH₃),     (4-Cl-5-CH₃), (6-Cl-5-CH₃), (2-Br-5-CH₃), (4-Br-5-CH₃),     (6-Br-5-CH₃), (2-OCH₃-5-CH₃), (4-OCH₃-5-CH₃), (6-OCH₃-5-CH₃),     (2-OCHF₂-5-CH₃), (4-OCHF₂-5-CH₃), (6-OCHF₂-5-CH₃), (2-F-5-CN),     (4-F-5-CN), (6-F-5-CN), (2-Cl-5-CN), (4-Cl-5-CN), (6-Cl-5-CN),     (2-Br-5-CN), (4-Br-5-CN), (6-Br-5-CN), (2-CH₃-5-CN), (4-CH₃-5-CN),     (6-CH₃-5-CN), (2-OCH₃-5-CN), (4-OCH₃-5-CN), (6-OCH₃-5-CN),     (2-OCHF₂-5-CN), (4-OCHF₂-5-CN), (6-OCHF₂-5-CN), (2-F-5-NO₂),     (4-F-5-NO₂), (6-F-5-NO₂), (2-Cl-5-NO₂), (4-Cl-5-NO₂), (6-Cl-5-NO₂),     (2-Br-5-NO₂), (4-Br-5-NO₂), (6-Br-5-NO₂), (2-CN-5-NO₂),     (4-CN-5-NO₂), (6-CN-5-NO₂), (2-CH₃-5-NO₂), (4-CH₃-5-NO₂),     (6-CH₃-5-NO₂), (2-OCH₃-5-NO₂), (4-OCH₃-5-NO₂), (6-OCH₃-5-NO₂),     (2-OCHF₂-5-NO₂), (4-OCHF₂-5-NO₂), (6-OCHF₂-5-NO₂), (2-F-5-CO₂CH₃),     (4-F-5-CO₂CH₃), (6-F-5-CO₂CH₃), (2-Cl-5-CO₂CH₃), (4-Cl-5-CO₂CH₃),     (6-Cl-5-CO₂CH₃), (2-Br-5-CO₂CH₃), (4-Br-5-CO₂CH₃), (6-Br-5-CO₂CH₃),     (2-CN-5-CO₂CH₃), (4-CN-5-CO₂CH₃), (6-CN-5-CO₂CH₃), (2-CH₃-5-CO₂CH₃),     (4-CH₃-5-CO₂CH₃), (6-CH₃-5-CO₂CH₃), (2-OCH₃-5-CO₂CH₃),     (4-OCH₃-5-CO₂CH₃), (6-OCH₃-5-CO₂CH₃), (2-OCHF₂-5-CO₂CH₃),     (4-OCHF₂-5-CO₂CH₃) or (6-OCHF₂-5-CO₂CH₃).

More preference is here given to compounds of the formula (I) or salts thereof in which

-   (R¹)_(m) and R³ together represent 5-bromo, 5-chloro, 5-fluoro,     5-cyano, 5-methyl, 5-ethyl, 5-CF₃, 5-methoxy, 5-nitro,     5-methoxycarbonyl, 5-ethoxycarbonyl, 2,5-difluoro, 4,5-difluoro,     5,6-difluoro, 5,6-dichloro, 5,6-dibromo, 5,6-dimethyl, 5,6-dicyano,     (6-Cl-5-F), (6-Br-5-F), (2-F-5-Cl), (4-F-5-Cl), (6-F-5-Cl),     (2-F-5-Br), (4-F-5-Br), (6-F-5-Br), (6-Br-5-Cl), (6-Cl-5-Br),     (6-CN-5-F), (6-CH₃-5-F), (6-OCH₃-5-F), (6-OCHF₂-5-F), (6-CN-5-Cl),     (6-CH₃-5-Cl), (6-OCH₃-5-Cl), (6-OCHF₂-5-Cl), (6-CN-5-Br),     (6-CH₃-5-Br), (6-OCH₃-5-Br), (6-OCHF₂-5-Br), (6-CN-5-CH₃),     (2-F-5-CH₃), (4-F-5-CH₃), (6-F-5-CH₃), (6-Cl-5-CH₃), (6-Br-5-CH₃),     (6-OCH₃-5-CH₃), (6-OCHF₂-5-CH₃), (2-F-5-CN), (4-F-5-CN), (6-F-5-CN),     (6-Cl-5-CN), (6-Br-5-CN), (6-CH₃-5-CN), (6-OCH₃-5-CN),     (6-OCHF₂-5-CN), (2-F-5-NO₂), (4-F-5-NO₂), (6-F-5-NO₂), (6-Cl-5-NO₂),     (6-Br-5-NO₂), (6-CN-5-NO₂), (6-CH₃-5-NO₂), (6-OCH₃-5-NO₂),     (6-OCHF₂-5-NO₂), (2-F-5-CO₂CH₃), (4-F-5-CO₂CH₃), (6-F-5-CO₂CH₃),     (6-Cl-5-CO₂CH₃), (6-Br-5-CO₂CH₃), (6-CN-5-CO₂CH₃), (6-CH₃-5-CO₂CH₃),     (6-OCH₃-5-CO₂CH₃) or (6-OCHF₂-5-CO₂CH₃).

More preference is given to:

Compounds of the formula (I) or salts thereof in which m=0 and (R²)_(n) represents 3-chloro, 4-chloro, 2-fluoro, 3-fluoro, 4-fluoro, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, (3-Cl-2-F), (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F) or (4-Cl-3-F) or else (2,6-difluoro-4-Cl), 3-cyano, 4-cyano, 3-nitro or 4-nitro and R³ represents fluorine, chlorine, bromine, methyl, cyano, nitro or methoxycarbonyl. Compounds of the formula (I) or salts thereof in which (R¹)_(m)=2-F, 2-Cl, 4-F, 4-Cl, 6-F, 6-Cl, 2-Br, 4-Br, 6-Br, 2-CN, 4-CN, 6-CN, 2-methyl, 4-methyl, 6-methyl, 2-ethyl, 4-ethyl, 6-ethyl, 2-methoxy, 4-methoxy, 6-methoxy, 2-ethoxy, 4-ethoxy, 6-ethoxy, 2-difluoromethoxy, 4-difluoromethoxy, 6-difluoromethoxy, 2-trifluoromethoxy, 4-trifluoromethoxy or 6-trifluoromethoxy and (R²)_(n) represents 3-chloro, 4-chloro, 2-fluoro, 3-fluoro, 4-fluoro, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, (3-Cl-2-F), (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F) or (4-Cl-3-F) or else (2,6-difluoro-4-Cl), 3-cyano, 4-cyano, 3-nitro or 4-nitro and R³ represents fluorine, chlorine, bromine, methyl, cyano, nitro, methoxycarbonyl or ethoxycarbonyl. Compounds of the formula (I) or salts thereof in which (R¹)_(m)=2-F, 2-Cl, 4-F, 4-Cl, 6-F, 6-Cl, 6-Br, 6-CN, 6-methyl, 6-methoxy or 6-difluoromethoxy and (R²)_(n) represents 3-chloro, 4-chloro, 2-fluoro, 3-fluoro, 4-fluoro, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, (3-Cl-2-F), (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F) or (4-Cl-3-F) or else (2,6-difluoro-4-Cl), 3-cyano, 4-cyano, 3-nitro or 4-nitro and R³ represents fluorine, chlorine, bromine, methyl, cyano, nitro or methoxycarbonyl.

In general, from among the compounds having the abovementioned meanings for individual groups or combinations of groups (R¹)_(m), (R²)_(n) and R³, preference is given to those in which the remaining groups or combinations of groups in the compounds are defined according to the meanings mentioned as preferred.

Preference is also given to compounds (I) in which

-   M represents an equivalent of a cation, preferably a metal ion     equivalent, an ammonium ion which is optionally substituted by 1 to     4 identical or different radicals from the group consisting of     (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl, phenyl,     (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl and phenyl-(C₁-C₄)-alkyl, in     particular (C₁-C₄)-alkyl, or a tertiary sulphonium ion which is     preferably substituted by 3 identical or different radicals from the     group consisting of (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl, phenyl,     (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl and phenyl-(C₁-C₄)-alkyl, in     particular (C₁-C₄)-alkyl.

Preference is given to the compounds of the formula (I) according to the invention, preferably of the formula (Ia), or salts thereof in which

-   R⁴ represents hydrogen, alkyl, alkenyl or alkynyl, where each of the     3 last-mentioned radicals is unsubstituted or substituted and,     including substituents, has up to 30 carbon atoms, preferably up to     24 carbon atoms, in particular up to 20 carbon atoms, or -    represents cycloalkyl, cycloalkenyl, cycloalkynyl or aryl, where     each of the 4 last-mentioned radicals is unsubstituted or     substituted and, including substituents, has up to 30 carbon atoms,     preferably up to 24 carbon atoms, in particular up to 20 carbon     atoms, or -    represents a heterocyclyl radical having 3 to 9 ring atoms which     contains 1 to 4 heteroatoms from the group consisting of N, O and S,     which is unsubstituted or substituted and which, including     substituents, has 1 to 30 carbon atoms, preferably 1 to 24 carbon     atoms, in particular 1 to 20 carbon atoms.

More preference is here also given to compounds (I), preferably of the formula (Ia), or salts thereof in which R⁴ represents hydrogen.

More preference is here also given to compounds (I), preferably of the formula (Ia), or salts thereof in which

-   R⁴ represents H, (C₁-C₁₈)-alkyl, (C₂-C₁₈)-alkenyl or     (C₂-C₁₈)-alkynyl, where each of the 3 last-mentioned radicals is     unsubstituted or substituted and, including substituents, has up to     30 carbon atoms, preferably up to 24 carbon atoms, in particular up     to 20 carbon atoms, or -    represents (C₃-C₉)-cycloalkyl, (C₅-C₉)-cycloalkenyl,     (C₅-C₉)-cycloalkynyl or phenyl, where each of the 4 last-mentioned     radicals is unsubstituted or substituted and, including     substituents, has up to 30 carbon atoms, preferably up to 24 carbon     atoms, in particular up to 20 carbon atoms.

More preference is here also given to compounds (I), preferably of the formula (Ia), or salts thereof in which

-   R⁴ represents hydrogen, (C₁-C₁₈)-alkyl, (C₂-C₁₈)-alkenyl or     (C₂-C₁₈)-alkynyl, where each of the 3 last-mentioned radicals is     unsubstituted or substituted by one or more radicals from the group     consisting of the radicals [subgroups (a)-(d)]     -   (a) halogen, cyano, thio, nitro, hydroxy, carboxy,         (C₁-C₈)-alkoxy, (C₂-C₈)-alkenyloxy, (C₂-C₈)-alkynyloxy,         (C₁-C₈)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,         (C₁-C₈)-alkylthio, (C₂-C₈)-alkenylthio, (C₂-C₈)-alkynylthio,         (C₁-C₈)-haloalkylthio, (C₂-C₈)-haloalkenylthio,         (C₂-C₈)-haloalkynylthio, (C₁-C₈)-alkylsulphinyl,         (C₂-C₈)-alkenylsulphinyl, (C₂-C₈)-alkynylsulphinyl,         (C₁-C₈)-haloalkylsulphinyl, (C₂-C₈)-haloalkenylsulphinyl,         (C₂-C₈)-haloalkynylsulphinyl, (C₁-C₈)-alkylsulphonyl,         (C₂-C₈)-alkenylsulphonyl, (C₂-C₈)-alkynylsulphonyl,         (C₁-C₈)-haloalkylsulphonyl, (C₂-C₈)-haloalkenylsulphonyl,         (C₂-C₈)-haloalkynylsulphonyl, radicals of the formula —NR*R**,         where R* and R** are defined as above or below, and         (C₃-C₈)-cycloalkyl, (C₅-C₈)-cycloalkenyl, (C₅-C₈)-cycloalkynyl,         (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxy,         (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkyl-S(O)_(p)—,         (C₅-C₈)-cycloalkenyl-(C₁-C₆)-alkoxy,         (C₅-C₈)-cycloalkenyl-(C₁-C₆)-alkyl-S(O)_(p)—,         (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkoxy,         (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkyl-S(O)_(p)—,         (C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkyl-S(O)_(p)—,         (C₅-C₈)-cycloalkenyloxy, (C₅-C₈)-cycloalkenyl-S(O)_(p)—,         (C₅-C₈)cycloalkynyloxy, (C₅-C₈)-cycloalkynyl-S(O)_(p)—,         (C₃-C₈)-cycloalkoxy-(C₁-C₆)-alkoxy,         (C₃-C₈)-cycloalkoxy-(C₁-C₆)-alkyl-S(O)_(p)—, phenyl,         phenyl-(C₁-C₆)-alkoxy, phenoxy, phenyl-S(O)_(p)—,         phenyl-(C₁-C₆)-alkyl-S(O)_(p)—, phenoxy-(C₁-C₆)-alkoxy,         phenoxy-(C₁-C₆)-alkyl-S(O)_(p)—, a radical Het⁷, Het⁷-S(O)_(p)—,         Het⁷-(C₁-C₆)-alkoxy, Het⁷-O—, Het⁷-O—(C₁-C₆)-alkoxy, where the         heterocyclic radical Het⁷ is defined as above or below,     -    where each of the 29 last-mentioned radicals is unsubstituted         in the acyclic moiety or substituted by one or more identical or         different radicals R^(A) and is unsubstituted in the cyclic         moiety or substituted by one or more identical or different         radicals R^(B) and p independently of the others in each case         represents 0, 1 or 2, and     -    preferably the radicals (a)     -    halogen, cyano, nitro, hydroxy, carboxy, (C₁-C₆)-alkoxy,         (C₁-C₈)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,         (C₁-C₆)-alkylthio, (C₁-C₆)-haloalkylthio,         (C₁-C₆)-alkylsulphinyl, (C₁-C₆)-haloalkylsulphinyl,     -    (C₁-C₆)-alkylsulphonyl, (C₁-C₈)-haloalkylsulphonyl,     -    (C₃-C₈)-cycloalkyl,     -    (C₅-C₈)-cycloalkenyl,     -    (C₅-C₈)-cycloalkynyl,     -    (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxy,     -    (C₅-C₈)-cycloalkenyl-(C₁-C₆)-alkoxy,     -    (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkoxy,     -    (C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkylthio,     -    (C₃-C₈)-cycloalkylsulphinyl, (C₃-C₈)-cycloalkylsulphonyl, -    (C₃-C₈)-cycloalkoxy-(C₁-C₆)-alkoxy,     -    phenyl, phenoxy, phenylthio, phenylsulphinyl, phenylsulphonyl,     -    phenyl-(C₁-C₆)-alkoxy, phenyl-(C₁-C₆)-alkylthio,     -    phenyl-(C₁-C₆)-alkylsulphinyl, phenyl-(C₁-C₆)-alkylsulphonyl,     -    phenoxy-(C₁-C₆)-alkoxy, phenoxy-(C₁-C₆)-alkylthio,     -    phenoxy-(C₁-C₆)-alkylsulphinyl and         phenoxy-(C₁-C₆)-alkylsulphyl,         -   where each of the radicals mentioned with cyclic moieties is             unsubstituted in the acyclic moiety or substituted by one or             more identical or different radicals R^(A) and is             unsubstituted in the cyclic moiety or substituted by one or             more identical or different radicals R^(B),     -   (b) radicals of the formulae —C(═O)—R^(C), —C(═O)—O—R^(C),         —O—C(═O)—R^(C), —O—C(═O)—O—R^(C), —C(═O)—S—R^(C),         —C(═S)—S—R^(C), —C(═S)—S—R^(C), —C(═O)—NR*R**, —C(═O)—O—NR*R**,         —O—C(═O)—NR*R**, —N(R*)—C(═O)—R^(C), —N(R*)—C(═O)—NR*R**,         —N(R*)—C(═O)—O—R^(C), —P(═O)(R^(C))(R^(D)),         —P(═O)(OR^(c))(R^(D)), —P(═O)(OR^(c))(OR^(D)) or         —O—P(═O)(OR^(c))(OR^(D)), preferably a radical of the formula         —C(═O)—R^(C), —C(═O)—O—R^(C), —O—C(═O)—R^(c) or         —O—C(═O)—O—R^(C), in particular a radical of the formula         —C(═O)—O—R^(C), —O—C(═O)—R^(c) or —O—C(═O)—O—R^(C),     -    where R*, R**, R^(C) and R^(D) are as defined below,     -    preferably the radicals (b1)     -    [(C₁-C₈)-alkoxy]carbonyl, [(C₁-C₈)-alkoxy]thiocarbonyl,         [(C₂-C₈)-alkenyloxy]carbonyl, [(C₂-C₈)-alkynyloxy]carbonyl,         [(C₁-C₈)-alkylthio]carbonyl, [(C₂-C₈)-alkenylthio]carbonyl,         [(C₂-C₈)-alkynylthio]carbonyl, (C₁-C₈)-alkanoyl,         [(C₂-C₈)-alkenyl]carbonyl, [(C₂-C₈)-alkynyl]carbonyl,         [(C₁-C₈)-alkyl]carbonylamino, [(C₂-C₈)-alkenyl]carbonylamino,         [(C₂-C₈)-alkynyl]carbonylamino, [(C₁-C₆)-alkoxy]carbonylamino,         [(C₂-C₈)-alkenyloxy]carbonylamino,         [(C₂-C₈)-alkynyloxy]carbonylamino,         [(C₁-C₈)-alkylamino]carbonylamino, [(C₁-C₆)-alkyl]carbonyloxy,         [(C₂-C₆)-alkenyl]carbonyloxy, [(C₂-C₆)-alkynyl]carbonyloxy,         [(C₁-C₈)-alkoxy]carbonyloxy, [(C₂-C₈)-alkenyloxy]carbonyloxy and         [(C₂-C₈)-alkynyloxy]carbonyloxy,     -    where each of the 23 last-mentioned radicals is unsubstituted         or substituted by one or more radicals from the group consisting         of halogen, NO₂, (C₁-C₄)-alkoxy and optionally halogen-, CN,         NO₂—, (C₁-C₄)-alkyl-, (C₁-C₄)-alkoxy- and         (C₁-C₄)-alkylthio-substituted phenyl, and preferably the         radicals (b2)     -    (C₃-C₈)-cycloalkylcarbonyl,     -    (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkyl]carbonyl,     -    (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkoxy]carbonyl,     -    (C₃-C₈)-cycloalkoxycarbonyl,     -    (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkyl]carbonyl,     -    (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkoxy]carbonyl,     -    (C₃-C₈)-cycloalkylcarbonyloxy,     -    (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkyl]carbonyloxy,     -    (C₅-C₈)-cycloalkenyl-[(C₁-C₆)-alkyl]carbonyloxy,     -    (C₅-C₈)-cycloalkynyl-[(C₁-C₆)-alkyl]carbonyloxy,     -    (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkoxy]carbonyloxy,     -    (C₅-C₈)-cycloalkenyl-[(C₁-C₆)-alkoxy]carbonyloxy,     -    (C₅-C₈)-cycloalkynyl-[(C₁-C₆)-alkoxy]carbonyloxy,     -    (C₃-C₈)-cycloalkoxycarbonyloxy,     -    (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkyl]carbonyloxy,     -    (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkoxy]carbonyloxy,     -    (C₃-C₈)-cycloalkylcarbonylamino,     -    (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkyl]carbonylamino,     -    (C₅-C₈)-cycloalkenyl-[(C₁-C₆)-alkyl]carbonylamino,     -    (C₅-C₈)-cycloalkynyl-[(C₁-C₆)-alkyl]carbonylamino,     -    (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkoxy]carbonylamino,     -    (C₃-C₈)-cycloalkoxycarbonylamino,     -    (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkyl]carbonylamino and     -    (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkoxy]carbonylamino,     -    phenylcarbonyl,     -    phenyl-[(C₁-C₆)-alkyl]carbonyl,     -    phenyl-[(C₁-C₆)-alkoxy]carbonyl,     -    phenoxycarbonyl,     -    phenoxy-[(C₁-C₆)-alkyl]carbonyl,     -    phenoxy-[(C₁-C₆)-alkoxy]carbonyl,     -    phenylcarbonyloxy,     -    phenyl-[(C₁-C₆)-alkyl]carbonyloxy,     -    phenyl-[(C₁-C₆)-alkoxy]carbonyloxy,     -    phenoxycarbonyloxy,     -    phenoxy-[(C₁-C₆)-alkyl]carbonyloxy,     -    phenoxy-[(C₁-C₆)-alkoxy]carbonyloxy,     -    phenylcarbonylamino,     -    phenyl-[(C₁-C₆)-alkyl]carbonylamino,     -    phenyl-[(C₁-C₆)-alkoxy]carbonylamino,     -    phenoxycarbonylamino,     -    phenoxy-[(C₁-C₆)-alkyl]carbonylamino,     -    phenoxy-[(C₁-C₆)-alkoxy]carbonylamino,     -    where each of the 42 last-mentioned radicals is optionally         fused in the cyclic moiety with a carbocyclic or heterocyclic         ring, preferably a carbocyclic ring having 3 to 6 carbon atoms         or a heterocyclic ring having 5 or 6 ring atoms and 1 to 3 ring         heteroatoms from the group consisting of N, O and S, preferably         benzo-fused, and unsubstituted at the ring or at the polycyclic         system or substituted by one or more radicals from the group         consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy,         (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy and nitro, and     -   (c) radicals of the formulae —SiR′₃, —O—SiR′₃,         (R′)₃Si—(C₁-C₆)-alkoxy, —CO—O—NR′₂, —O—N═CR′₂, —N═CR′₂, —O—NR′₂,         —CH(OR′)₂ and —O—(CH₂)_(q)—CH(OR)₂, in which each of the         radicals R′ independently of the others represents H,         (C₁-C₄)-alkyl or phenyl, which is unsubstituted or substituted         by one or more radicals from the group consisting of halogen,         (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,         (C₁-C₄)-haloalkoxy and nitro or at two adjacent positions by a         (C₂-C₆)-alkylene bridge, and q represents an integer from 0 to         6, and     -   (d) radicals of the formula R″O—CHR′″CH(OR″)—(C₁-C₆)-alkoxy,     -    in which each of the radicals R″ independently of the others         represents H or (C₁-C₄)-alkyl or together the radicals represent         a (C₁-C₆)-alkylene group and R′″ represents H or (C₁-C₄)-alkyl,     -   or -   R⁴ represents (C₃-C₉)-cycloalkyl, (C₅-C₉)-cycloalkenyl,     (C₅-C₉)-cycloalkynyl or phenyl, -    where each of the 4 last-mentioned radicals is unsubstituted or     substituted by one or more radicals from the group consisting of the     radicals [subgroups (a′)-(e′)]     -   (a′) halogen, cyano, thio, nitro, hydroxy, carboxy,         (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,         (C₂-C₈)-alkenyl, (C₂-C₈)-haloalkenyl, (C₂-C₈)-alkynyl,         (C₂-C₈)-haloalkynyl, (C₁-C₈)-alkoxy, (C₂-C₈)-alkenyloxy,         (C₂-C₈)-alkynyloxy, (C₁-C₈)-haloalkoxy,         (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₈)-alkylthio,         (C₂-C₈)-alkenylthio, (C₂-C₈)-alkynylthio and radicals of the         formulae —NR*R**, where the radicals R* and R** are defined         below,     -   (b′) radicals of the formulae —C(═O)—R^(C), —C(═O)—O—R^(C),         —O—C(═O)—R^(C), —O—C(═O)—O—R^(C), —C(═O)—S—R^(C),         —C(═S)—S—R^(C), —C(═S)—S—R^(C), —C(═O)—NR*R**, —C(═O)—O—NR*R**,         —O—C(═O)—NR*R**, —N(R*)—C(═O)—R^(C), —N(R*)—C(═O)—NR*R**,         —N(R*)—C(═O)—O—R^(C), —P(═O)(R^(C))(R^(D)),         —P(═O)(OR^(c))(R^(D)), —P(═O)(OR^(c))(OR^(D)) and         —O—P(═O)(OR^(c))(OR^(D)),     -    preferably a radical of the formula —C(═O)—R^(C),         —C(═O)—O—R^(C), —O—C(═O)—R^(c) or —O—C(═O)—O—R^(C), in         particular a radical of the formula —C(═O)—O—R^(C),         —O—C(═O)—R^(c) or —O—C(═O)—O—R^(C),     -    where R*, R**, R^(C) and R^(D) are as defined below,     -    and preferably the radicals (b1′)     -    [(C₁-C₈)-alkoxy]carbonyl, [(C₁-C₈)-alkoxy]thiocarbonyl,         [(C₂-C₈)-alkenyloxy]carbonyl, [(C₂-C₈)-alkynyloxy]carbonyl,         [(C₁-C₈)-alkylthio]carbonyl, [(C₂-C₈)-alkenylthio]carbonyl,         [(C₂-C₈)-alkynylthio]carbonyl, (C₁-C₈)-alkanoyl,         [(C₂-C₈)-alkenyl]carbonyl, [(C₂-C₈)-alkynyl]carbonyl,         (C₁-C₄)-alkylimino, (C₁-C₄)-alkoxyimino,         [(C₁-C₈)-alkyl]carbonylamino, [(C₂-C₈)-alkenyl]carbonylamino,         [(C₂-C₈)-alkynyl]carbonylamino, [(C₁-C₈)-alkoxy]carbonylamino,         [(C₂-C₈)-alkenyloxy]carbonylamino,         [(C₂-C₈)-alkynyloxy]carbonylamino,         [(C₁-C₈)-alkylamino]carbonylamino, [(C₁-C₆)-alkyl]carbonyloxy,         [(C₂-C₆)-alkenyl]carbonyloxy, [(C₂-C₆)-alkynyl]carbonyloxy,         [(C₁-C₈)-alkoxy]carbonyloxy, [(C₂-C₈)-alkenyloxy]carbonyloxy,         [(C₂-C₈)-alkynyloxy]carbonyloxy, (C₁-C₈)-alkylsulphinyl and         (C₁-C₈)-alkylsulphonyl, where each of the 27 last-mentioned         radicals is unsubstituted or substituted by one or more radicals         from the group consisting of halogen, NO₂, (C₁-C₄)-alkoxy and         optionally substituted phenyl, and preferably the radicals (b2′)     -    (C₃-C₈)-cycloalkylcarbonyl,     -    (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkyl]carbonyl,     -    (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkoxy]carbonyl,     -    (C₃-C₈)-cycloalkoxycarbonyl,     -    (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkyl]carbonyl,     -    (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkoxy]carbonyl,     -    (C₃-C₈)-cycloalkylcarbonyloxy,     -    (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkyl]carbonyloxy,     -    (C₅-C₈)-cycloalkenyl-[(C₁-C₆)-alkyl]carbonyloxy,     -    (C₅-C₈)-cycloalkynyl-[(C₁-C₆)-alkyl]carbonyloxy,     -    (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkoxy]carbonyloxy,     -    (C₅-C₈)-cycloalkenyl-[(C₁-C₆)-alkoxy]carbonyloxy,     -    (C₅-C₈)-cycloalkynyl-[(C₁-C₆)-alkoxy]carbonyloxy,     -    (C₃-C₈)-cycloalkoxycarbonyloxy,     -    (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkyl]carbonyloxy,     -    (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkoxy]carbonyloxy,     -    (C₃-C₈)-cycloalkylcarbonylamino,     -    (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkyl]carbonylamino,     -    (C₅-C₈)-cycloalkenyl-[(C₁-C₆)-alkyl]carbonylamino,     -    (C₅-C₈)-cycloalkynyl-[(C₁-C₆)-alkyl]carbonylamino,     -    (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkoxy]carbonylamino,     -    (C₃-C₈)-cycloalkoxycarbonylamino,     -    (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkyl]carbonylamino and     -    (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkoxy]carbonylamino,     -    phenylcarbonyl,     -    phenyl-[(C₁-C₆)-alkyl]carbonyl,     -    phenyl-[(C₁-C₆)-alkoxy]carbonyl,     -    phenoxycarbonyl,     -    phenoxy-[(C₁-C₆)-alkyl]carbonyl,     -    phenoxy-[(C₁-C₆)-alkoxy]carbonyl,     -    phenylcarbonyloxy,     -    phenyl-[(C₁-C₆)-alkyl]carbonyloxy,     -    phenyl-[(C₁-C₆)-alkoxy]carbonyloxy,     -    phenoxycarbonyloxy,     -    phenoxy-[(C₁-C₆)-alkyl]carbonyloxy,     -    phenoxy-[(C₁-C₆)-alkoxy]carbonyloxy,     -    phenylcarbonylamino,     -    phenyl-[(C₁-C₆)-alkyl]carbonylamino,     -    phenyl-[(C₁-C₆)-alkoxy]carbonylamino,     -    phenoxycarbonylamino,     -    phenoxy-[(C₁-C₆)-alkyl]carbonylamino,     -    phenoxy-[(C₁-C₆)-alkoxy]carbonylamino,     -    where each of the 42 last-mentioned radicals is optionally         fused in the cyclic moiety with a carbocyclic or heterocyclic         ring, preferably a carbocyclic ring having 3 to 6 carbon atoms         or a heterocyclic ring having 5 or 6 ring atoms and 1 to 3 ring         heteroatoms from the group consisting of N, O and S, preferably         benzo-fused, and unsubstituted at the ring or at the polycyclic         system or substituted by one or more radicals from the group         consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy,         (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy and nitro, and     -   (c′) radicals of the formulae —SiR′₃, —O—SiR′₃,         (R′)₃Si—(C₁-C₆)-alkoxy, —CO—O—NR′₂, —O—N═CR′₂, —N═CR′₂, —O—NR′₂,         —CH(OR′)₂ and —O—(CH₂)q-CH(OR′)₂,     -    in which each of the radicals R′ independently of the others         represents H, (C₁-C₄)-alkyl or phenyl, which is unsubstituted or         substituted by one or more radicals from the group consisting of         halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,         (C₁-C₄)-haloalkoxy and nitro or at two adjacent positions by a         (C₂-C₆)-alkylene bridge, and q represents an integer from 0 to         6, and     -   (d′) radicals of the formula R″O—CHR′″CH(OR″)—(C₁-C₆)-alkoxy,     -    in which each of the radicals R″ independently of the others is         H or (C₁-C₄)-alkyl or together the radicals are a         (C₁-C₆)-alkylene group and R′″ is H or (C₁-C₄)-alkyl, and     -   (e′) a radical of the formula Het⁷ which is unsubstituted or         substituted by one or more identical or different radicals         R^(B),     -   or -   R⁴ represents a polycyclic radical based on (C₃-C₉)-cycloalkyl,     (C₅-C₉)-cycloalkenyl, (C₅-C₉)-cycloalkynyl or phenyl, where the base     ring is fused with a carbocyclic or heterocyclic ring, preferably a     5- or 6-membered ring having 0 or 1 to 3 ring heteroatoms from the     group consisting of N, O and S, preferably benzo-fused, and where     the base ring or the polycyclic system is unsubstituted or     substituted by one or more identical or different radicals R^(B),     preferably unsubstituted or substituted by one or more radicals from     the group consisting of halogen, cyano, nitro, hydroxy, carboxy,     (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,     (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,     (C₂-C₆)-haloalkynyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy,     (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkoxy,     (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₆)-alkylthio,     (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₃-C₆)-cycloalkyl,     (C₃-C₆)-cycloalkoxy, [(C₁-C₈)-alkoxy]carbonyl,     [(C₁-C₆)-haloalkoxy]carbonyl and oxo, or -   R⁴ represents a heterocyclic radical Het⁷ which is unsubstituted in     the ring or in the polycyclic system or substituted by one or more     identical or different radicals R^(B), preferably unsubstituted or     substituted by one or more radicals from the group consisting of     halogen, cyano, thio, nitro, hydroxy, carboxy, (C₁-C₆)-alkyl,     (C₁-C₆)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₂-C₆)-alkenyl,     (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,     (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy,     (C₁-C₆)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,     (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio,     (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkoxy, [(C₁-C₈)-alkoxy]carbonyl,     [(C₁-C₆)-haloalkoxy]carbonyl and oxo, -   where in the radicals mentioned above and in the radicals below -   Het⁷ in each case independently of the others is a saturated,     partially unsaturated or heteroaromatic monocyclic heterocyclyl     radical having 3 to 9 ring atoms, preferably having 5 or 6 ring     atoms, or a 9- or 10-membered bicyclic heterocycle which contains 1,     2, 3 or 4 heteroatoms selected from the group consisting of O, N and     S, preferably a 5- or 6-membered heterocycle having 1 to 3 ring     heteroatoms from the group consisting of N, O and S which is     optionally also fused to a carbocyclic or heterocyclic ring,     preferably a carbocyclic ring having 3 to 6 carbon atoms or a     heterocyclic ring having 5 or 6 ring atoms and 1 to 3 ring     heteroatoms from the group consisting of N, O and S, preferably     optionally benzo-fused, -   R*, R** independently of one another (i.e. also of other groups     NR*R**) each represent H, (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl,     (C₂-C₈)-alkynyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-alkanoyl,     [(C₁-C₄)-haloalkyl]carbonyl, [(C₁-C₄)-alkoxy]carbonyl,     [(C₁-C₄)-haloalkoxy]carbonyl, (C₃-C₆)-cycloalkyl,     (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl, phenyl, phenyl-(C₁-C₄)-alkyl,     where each of the 4 last-mentioned radicals is optionally     substituted in the cycle by one or more identical or different     radicals R^(bb), or -   R* and R** together with the nitrogen atom represent a 3- to     8-membered heterocycle which, in addition to the nitrogen atom, may     contain one or two further ring heteroatoms from the group     consisting of N, O and S and which may be unsubstituted or     substituted by one or more radicals from the group consisting of     (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo, -   R^(A) represents halogen, cyano, hydroxy or (C₁-C₆)-alkoxy, -   R^(B) represents halogen, cyano, hydroxy, oxo, nitro, (C₁-C₆)-alkyl,     (C₁-C₄)-haloalkyl, cyano-(C₁-C₄)-alkyl, hydroxy-(C₁-C₄)-alkyl,     nitro-(C₁-C₄)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl,     (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₁-C₆)-alkoxy,     (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkoxy,     (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,     (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkoxy,     (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio,     (C₁-C₆)-alkylsulphinyl, (C₁-C₆)-haloalkylsulphinyl,     (C₁-C₆)-alkylsulphonyl, (C₁-C₆)-haloalkylsulphonyl, a radical of the     formula R^(aa)—C(═O)— or R^(aa)—C(═O)—(C₁-C₆)alkyl, the radicals     R^(aa) being defined below, —NR*R**, R* and R** being defined below,     tri-[(C₁-C₄)-alkyl]silyl, tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₆)-alkyl,     (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkoxy,     (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₈)-alkoxy,     phenyl, phenyl-(C₁-C₆)-alkyl, phenoxy, phenoxy-(C₁-C₆)-alkyl,     phenylamino, phenylamino-(C₁-C₆)-alkyl or a 5- or 6-membered     monocyclic or 9- or 10-membered bicyclic heterocycle which contains     1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N     and S, where each of the 11 last-mentioned radicals is optionally     substituted in the cyclic moiety by one or more identical or     different radicals R^(bb), -   R^(C), R^(D) are each independently of one another (also     independently of radicals R^(C), R^(D) in other groups)     -   hydrogen, (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl or (C₂-C₈)-alkynyl,         where each of the 3 last-mentioned radicals is unsubstituted or         substituted by one or more radicals from the group consisting of         halogen, cyano, nitro, hydroxy, (C₁-C₆)-alkoxy,         (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₈)-haloalkoxy,         (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₈)-alkylthio,         (C₁-C₈)-haloalkylthio, (C₁-C₈)-alkylsulphinyl,         (C₁-C₈)-haloalkylsulphinyl, (C₁-C₈)-alkylsulphonyl,         (C₁-C₈)-haloalkylsulphonyl and tri-[(C₁-C₄)-alkyl]silyl,     -   or     -   (C₃-C₈)-cycloalkyl, (C₅-C₈)-cycloalkenyl, (C₅-C₈)-cycloalkynyl,         phenyl, (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkyl,         (C₅-C₈)-cycloalkenyl-(C₁-C₆)-alkyl,         (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkyl, phenyl-(C₁-C₆)-alkyl,         (C₃-C₈)-cycloalkyloxy-(C₁-C₆)-alkyl,         (C₃-C₈)-cycloalkyl-S(O)_(p)—(C₁-C₆)-alkyl,         (C₅-C₈)-cycloalkenyloxy-(C₁-C₆)-alkyl,         (C₅-C₈)-cycloalkynyloxy-(C₁-C₆)-alkyl, phenoxy-(C₁-C₆)-alkyl,         phenyl-S(O)_(p)—(C₁-C₆)-alkyl,         (C₃-C₈)-cycloalkylamino-(C₁-C₆)-alkyl,         (C₅-C₈)-cycloalkenylamino-(C₁-C₆)-alkyl,         (C₅-C₈)-cycloalkynylamino-(C₁-C₆)-alkyl,         phenylamino-(C₁-C₆)-alkyl, Het⁷, Het⁷-(C₁-C₆)-alkyl,         Het⁷-O—(C₁-C₆)-alkyl or Het⁷-S(O)_(p)—(C₁-C₆)-alkyl, where Het⁷         has the meaning mentioned,         -   where each of the 22 last-mentioned radicals is             unsubstituted in the acyclic moiety or substituted by one or             more identical or different radicals R^(A) and is             unsubstituted in the cyclic moiety or substituted by one or             more identical or different radicals R^(B) and p             independently of the others in each case represents 0, 1 or             2, -   R^(aa) independently of one another each represent hydrogen, OH,     (C₁-C₆)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,     (C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,     (C₁-C₆)-alkoxy-(C₁-C₆)-alkyloxy, (C₁-C₄)-haloalkoxy,     (C₁-C₄)-haloalkoxy-(C₁-C₆)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₆)-alkoxy,     (C₃-C₆)-alkenyloxy, (C₃-C₆)-alkenyloxy-(C₁-C₆)-alkyl,     (C₃-C₆)-alkenyloxy-(C₁-C₆)-alkoxy, (C₃-C₆)-alkynyloxy,     (C₃-C₆)-alkynyloxy-(C₁-C₆)-alkyl, (C₃-C₆)-alkynyloxy-(C₁-C₆)-alkoxy,     —NR*R*, where R* and R** are as defined above,     tri-[(C₁-C₄)alkyl]silyl, tri-[(C₁-C₄)alkyl]silyl-(C₁-C₆)-alkyl,     tri-[(C₁-C₄)alkyl]silyl-(C₁-C₆)-alkoxy, (C₃-C₆)-cycloalkyl,     (C₃-C₆)-cycloalkoxy, (C₃-C₆)-cycloalkyl-(C₁-C₈)-alkyl,     (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkoxy, (C₅-C₆)-cycloalkenyl,     (C₅-C₆)-cycloalkenyl-(C₁-C₆)-alkyl, (C₅-C₆)-cycloalkenyloxy,     (C₅-C₆)-cycloalkynyl, (C₅-C₆)-cycloalkynyl-(C₁-C₆)-alkyl,     (C₅-C₆)-cycloalkynyl-(C₁-C₆)-alkoxy, phenyl, phenyl-(C₁-C₆)-alkyl,     phenyl-(C₁-C₆)-alkoxy, phenoxy, phenoxy-(C₁-C₆)-alkyl,     phenoxy-(C₁-C₆)-alkoxy, phenylthio, phenyl-S(O)_(p)—(C₁-C₆)-alkyl,     phenyl-S(O)_(p)—(C₁-C₆)-alkoxy, where p independently of the others     in each case represents 0, 1 or 2, phenylamino,     phenylamino-(C₁-C₁)-alkyl, phenylamino-(C₁-C₆)-alkoxy or a 5- or     6-membered monocyclic or 9- or 10-membered bicyclic heterocycle     which is optionally attached via an alkylene group or an alkoxy     group and contains 1, 2, 3 or 4 heteroatoms selected from the group     consisting of O, N and S, where each of the 20 last-mentioned     radicals is optionally substituted in the cyclic moiety by one or     more identical or different radicals R^(cc), and -   R^(bb) and R^(cc) independently of one another each represent     halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy or     (C₁-C₄)-haloalkoxy.

More preference is here also given to compounds (I), preferably of the formula (Ia), or salts thereof in which

-   R⁴ represents hydrogen, (C₁-C₁₈)-alkyl, (C₂-C₁₈)-alkenyl or     (C₂-C₁₈)-alkynyl, preferably H, (C₁-C₁₂)-alkyl, (C₂-C₁₂)-alkenyl or     (C₂-C₁₂)-alkynyl, in particular H, (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl or     (C₂-C₈)-alkynyl, more preferably H or (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl     or (C₂-C₆)-alkynyl, more preferably (C₁-C₄)-alkyl, where each of the     13 last-mentioned radicals containing carbon atoms is unsubstituted     or substituted by one or more radicals from the group consisting of     the radicals [subgroups (a)-(d)]     -   (a) halogen, cyano, thio, nitro, hydroxy, carboxy,         (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy,         (C₁-C₆)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,         (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio,         (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio,         (C₂-C₆)-haloalkynylthio, (C₁-C₆)-alkylsulphinyl,         (C₂-C₆)-alkenylsulphinyl, (C₂-C₆)-alkynylsulphinyl,         (C₁-C₆)-haloalkylsulphinyl, (C₂-C₆)-haloalkenylsulphinyl,         (C₂-C₆)-haloalkynylsulphinyl, (C₁-C₆)-alkylsulphonyl,         (C₂-C₆)-alkenylsulphonyl, (C₂-C₆)-alkynylsulphonyl,         (C₁-C₆)-haloalkylsulphonyl, (C₂-C₆)-haloalkenylsulphonyl,         (C₂-C₆)-haloalkynylsulphonyl, radicals of the formula —NR*R**,         where R* and R** are defined below, and (C₃-C₆)-cycloalkyl,         (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkynyl,         (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkoxy,         (C₅-C₆)-cycloalkenyl-(C₁-C₄)-alkoxy,         (C₅-C₆)-cycloalkynyl-(C₁-C₄)-alkoxy, (C₃-C₆)-cycloalkoxy,         (C₅-C₆)-cycloalkenyloxy, (C₅-C₆)-cycloalkynyloxy,         (C₃-C₆)-cycloalkoxy-(C₁-C₄)-alkoxy, phenyl,         phenyl-(C₁-C₆)-alkoxy, phenoxy, phenoxy-(C₁-C₄)-alkoxy,         phenyl-S(O)_(p)—, phenyl-(C₁-C₆)-alkyl-S(O)_(p)—,         phenyloxy-(C₁-C₆)-alkyl-S(O)_(p)—, a radical Het⁷,         Het⁷-(C₁-C₆)-alkoxy, Het⁷-O—, Het⁷-O—(C₁-C₄)-alkoxy,         Het⁷-(C₁-C₆)-alkoxy, Het⁷-S(O)_(p)—,         Het⁷-O—(C₁-C₄)-alkyl-S(O)_(p)—, where the heterocyclic radical         Het⁷ is defined as above or below,         -   where each of the 24 last-mentioned radicals is             unsubstituted in the acyclic moiety or substituted by one or             more identical or different radicals R^(A) and is             unsubstituted in the cyclic moiety or substituted by one or             more identical or different radicals R^(B) and p             independently of the others in each case represents 0, 1 or             2,     -    and     -    preferably the radicals (a1)     -    halogen, cyano, nitro, hydroxy, carboxy, (C₁-C₆)-alkoxy,         (C₁-C₆)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,         (C₁-C₆)-alkylthio, (C₁-C₆)-haloalkylthio,         (C₁-C₆)-alkylsulphinyl, (C₁-C₆)-haloalkylsulphinyl,         (C₃-C₆)-cycloalkyl, (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkynyl,         (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkoxy,         (C₅-C₄)-cycloalkenyl-(C₁-C₄)-alkoxy,         (C₅-C₄)-cycloalkynyl-(C₁-C₄)-alkoxy, (C₃-C₄)-cycloalkoxy,         (C₃-C₄)-cycloalkoxy-(C₁-C₄)-alkoxy, phenyl,         phenyl-(C₁-C₄)-alkoxy, phenoxy and phenoxy-(C₁-C₄)-alkoxy,         phenylthio, phenylsulphinyl, phenylsulphonyl,         -   where each of the radicals (a1) is unsubstituted in the             acyclic moiety or substituted by one or more identical or             different radicals R^(A) and is unsubstituted in the cyclic             moiety or substituted by one or more identical or different             radicals R^(B),     -   (b) radicals of the formulae —C(═O)—R^(C), —C(═O)—O—R^(C),         —O—C(═O)—R^(C), —O—C(═O)—O—R^(C), —C(═O)—S—R^(C),         —C(═S)—S—R^(C), —C(═S)—S—R^(C), —C(═O)—NR*R**, —C(═O)—O—NR*R**,         —O—C(═O)—NR*R**, —N(R*)—C(═O)—R^(C), —N(R*)—C(═O)—NR*R**,         —N(R*)—C(═O)—O—R^(C), —P(═O)(R^(C))(R^(D)),         —P(═O)(OR^(c))(R^(D)), —P(═O)(OR^(c))(OR^(D)) and         —O—P(═O)(OR^(c))(OR^(D)), preferably a radical of the formula         —C(═O)—R^(C), —C(═O)—O—R^(C), —O—C(═O)—R^(c) or         —O—C(═O)—O—R^(C), in particular a radical of the formula         —C(═O)—O—R^(C), —O—C(═O)—R^(c) or —O—C(═O)—O—R^(C),     -    where R*, R**, R^(C) and R^(D) are as defined below,     -    preferably the radicals (b1)     -    [(C₁-C₆)-alkoxy]carbonyl, [(C₁-C₆)-alkoxy]thiocarbonyl,         [(C₂-C₆)-alkenyloxy]carbonyl, [(C₂-C₈)-alkynyloxy]carbonyl,         [(C₁-C₆)-alkylthio]carbonyl, [(C₂-C₆)-alkenylthio]carbonyl,         [(C₂-C₆)-alkynylthio]carbonyl, (C₁-C₆)-alkanoyl,         [(C₂-C₆)-alkenyl]carbonyl, [(C₂-C₆)-alkynyl]carbonyl,         [(C₁-C₆)-alkyl]carbonylamino, [(C₂-C₆)-alkenyl]carbonylamino,         [(C₂-C₆)-alkynyl]carbonylamino, [(C₁-C₆)-alkoxy]carbonylamino,         [(C₂-C₆)-alkenyloxy]carbonylamino,         [(C₂-C₆)-alkynyloxy]carbonylamino,         [(C₁-C₆)-alkylamino]carbonylamino, [(C₁-C₆)-alkyl]carbonyloxy,         [(C₂-C₆)-alkenyl]carbonyloxy, [(C₂-C₆)-alkynyl]carbonyloxy,         [(C₁-C₆)-alkoxy]carbonyloxy, [(C₂-C₆)-alkenyloxy]carbonyloxy and         [(C₂-C₆)-alkynyloxy]carbonyloxy,     -    where each of the 23 last-mentioned radicals is unsubstituted         or substituted by one or more radicals from the group consisting         of halogen, NO₂, (C₁-C₄)-alkoxy and optionally halogen-, CN,         NO₂, (C₁-C₄)-alkyl-, (C₁-C₄)-alkoxy- and         (C₁-C₄)-alkylthio-substituted phenyl, and preferably the         radicals (b2)     -    (C₃-C₆)-cycloalkylcarbonyl,     -    (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkyl]carbonyl,     -    (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkoxy]carbonyl,     -    (C₃-C₆)-cycloalkoxycarbonyl,     -    (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkyl]carbonyl,     -    (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkoxy]carbonyl,     -    (C₃-C₆)-cycloalkylcarbonyloxy,     -    (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkyl]carbonyloxy,     -    (C₅-C₆)-cycloalkenyl-[(C₁-C₄)-alkyl]carbonyloxy,     -    (C₅-C₆)-cycloalkynyl-[(C₁-C₄)-alkyl]carbonyloxy,     -    (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkoxy]carbonyloxy,     -    (C₅-C₆)-cycloalkenyl-[(C₁-C₄)-alkoxy]carbonyloxy,     -    (C₅-C₆)-cycloalkynyl-[(C₁-C₄)-alkoxy]carbonyloxy,     -    (C₃-C₆)-cycloalkoxycarbonyloxy,     -    (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkyl]carbonyloxy,     -    (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkoxy]carbonyloxy,     -    (C₃-C₆)-cycloalkylcarbonylamino,     -    (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkyl]carbonylamino,     -    (C₅-C₆)-cycloalkenyl-[(C₁-C₄)-alkyl]carbonylamino,     -    (C₅-C₆)-cycloalkynyl-[(C₁-C₄)-alkyl]carbonylamino,     -    (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkoxy]carbonylamino,     -    (C₃-C₆)-cycloalkoxycarbonylamino,     -    (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkyl]carbonylamino and     -    (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkoxy]carbonylamino,     -    phenylcarbonyl,     -    phenyl-[(C₁-C₄)-alkyl]carbonyl,     -    phenyl-[(C₁-C₄)-alkoxy]carbonyl,     -    phenoxycarbonyl,     -    phenoxy-[(C₁-C₄)-alkyl]carbonyl,     -    phenoxy-[(C₁-C₄)-alkoxy]carbonyl,     -    phenylcarbonyloxy,     -    phenyl-[(C₁-C₄)-alkyl]carbonyloxy,     -    phenyl-[(C₁-C₄)-alkoxy]carbonyloxy,     -    phenoxycarbonyloxy,     -    phenoxy-[(C₁-C₄)-alkyl]carbonyloxy,     -    phenoxy-[(C₁-C₄)-alkoxy]carbonyloxy,     -    phenylcarbonylamino,     -    phenyl-[(C₁-C₄)-alkyl]carbonylamino,     -    phenyl-[(C₁-C₄)-alkoxy]carbonylamino,     -    phenoxycarbonylamino,     -    phenoxy-[(C₁-C₄)-alkyl]carbonylamino,     -    phenoxy-[(C₁-C₄)-alkoxy]carbonylamino,     -    where each of the 42 last-mentioned radicals is optionally         fused in the cyclic moiety with a carbocyclic or heterocyclic         ring, preferably a carbocyclic ring having 3 to 6 carbon atoms         or a heterocyclic ring having 5 or 6 ring atoms and 1 to 3 ring         heteroatoms from the group consisting of N, O and S, preferably         benzo-fused, and unsubstituted at the ring or at the polycyclic         system or substituted by one or more radicals from the group         consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy,         (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy and nitro, and     -   (c) radicals of the formulae —SiR′₃, —O—SiR′₃,         (R′)₃Si—(C₁-C₄)-alkoxy, —CO—O—NR′₂, —O—N═CR′₂, —N═CR′₂, —O—NR′₂,         —CH(OR′)₂ and —O—(CH₂)_(q)—CH(OH)₂, in which each of the         radicals R′ independently of the others represents H,         (C₁-C₄)-alkyl or phenyl, which is unsubstituted or substituted         by one or more radicals from the group consisting of halogen,         (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,         (C₁-C₄)-haloalkoxy and nitro or at two adjacent positions by a         (C₂-C₆)-alkylene bridge, and q represents an integer from 0 to         6, and     -   (d) radicals of the formula R″O—CHR′″CH(OR″)—(C₁-C₆)-alkoxy, in         which each of the radicals R″ independently of the others         represents H or (C₁-C₄)-alkyl or together the radicals represent         a (C₁-C₆)-alkylene group and R′″ represents H or (C₁-C₄)-alkyl,     -   or -   R⁴ represents (C₃-C₆)-cycloalkyl, (C₅-C₆)-cycloalkenyl,     (C₅-C₆)-cycloalkynyl or phenyl, -    where each of the 4 last-mentioned radicals is unsubstituted or     substituted by one or more radicals from the group consisting of the     radicals [subgroups (a′)-(e′)]     -   (a′) halogen, cyano, thio, nitro, hydroxy, carboxy,         (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,         (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,         (C₂-C₆)-haloalkynyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy,         (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkoxy,         (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₆)-alkylthio,         (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio and radicals of the         formulae —NR*R**, where the radicals R* and R** are as defined         above or below,     -   (b′) radicals of the formulae —C(═O)—R^(C), —C(═O)—O—R^(C),         —O—C(═O)—R^(C), —O—C(═O)—O—R^(C), —C(═O)—S—R^(C),         —C(═S)—S—R^(C), —C(═S)—S—R^(C), —C(═O)—NR*R**, —C(═O)—O—NR*R**,         —O—C(═O)—NR*R**, —N(R*)—C(═O)—R^(C), —N(R*)—C(═O)—NR*R**,         —N(R*)—C(═O)—O—R^(C), —P(═O)(R^(C))(R^(D)),         —P(═O)(OR^(c))(R^(D)), —P(═O)(OR^(c))(OR^(D)) and         —O—P(═O)(OR^(c))(OR^(D)), preferably a radical of the formula         —C(═O)—R^(C), —C(═O)—O—R^(C), —O—C(═O)—R^(c) or         —O—C(═O)—O—R^(C), in particular a radical of the formula         —C(═O)—O—R^(C), —O—C(═O)—R^(c) or —O—C(═O)—O—R^(C),     -    where R*, R**, R^(C) and R^(D) are as defined below,     -    and preferably the radicals (b1′)     -    [(C₁-C₆)-alkoxy]carbonyl, [(C₁-C₆)-alkoxy]thiocarbonyl,         [(C₂-C₆)-alkenyloxy]carbonyl, [(C₂-C₆)-alkynyloxy]carbonyl,         [(C₁-C₆)-alkylthio]carbonyl, [(C₂-C₆)-alkenylthio]carbonyl,         [(C₂-C₆)-alkynylthio]carbonyl, (C₁-C₈)-alkanoyl,         [(C₂-C₆)-alkenyl]carbonyl, [(C₂-C₆)-alkynyl]carbonyl,         (C₁-C₄)-alkylimino, (C₁-C₄)-alkoxyimino,         [(C₁-C₆)-alkyl]carbonylamino, [(C₂-C₆)-alkenyl]carbonylamino,         [(C₂-C₆)-alkynyl]carbonylamino, [(C₁-C₆)-alkoxy]carbonylamino,         [(C₂-C₆)-alkenyloxy]carbonylamino,         [(C₂-C₆)-alkynyloxy]carbonylamino,         [(C₁-C₆)-alkylamino]carbonylamino, [(C₁-C₄)-alkyl]carbonyloxy,         [(C₂-C₄)-alkenyl]carbonyloxy, [(C₂-C₄)-alkynyl]carbonyloxy,         [(C₁-C₆)-alkoxy]carbonyloxy, [(C₂-C₆)-alkenyloxy]carbonyloxy,         [(C₂-C₆)-alkynyloxy]carbonyloxy, (C₁-C₆)-alkylsulphinyl and         (C₁-C₆)-alkylsulphonyl,     -    where each of the 27 last-mentioned radicals is unsubstituted         or substituted by one or more radicals from the group consisting         of halogen, NO₂, (C₁-C₄)-alkoxy and optionally substituted         phenyl, and preferably the radicals (b2′)     -    (C₃-C₆)-cycloalkylcarbonyl,     -    (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkyl]carbonyl,     -    (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkoxy]carbonyl,     -    (C₃-C₆)-cycloalkoxycarbonyl,     -    (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkyl]carbonyl,     -    (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkoxy]carbonyl,     -    (C₃-C₆)-cycloalkylcarbonyloxy,     -    (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkyl]carbonyloxy,     -    (C₅-C₆)-cycloalkenyl-[(C₁-C₄)-alkyl]carbonyloxy,     -    (C₅-C₆)-cycloalkynyl-[(C₁-C₄)-alkyl]carbonyloxy,     -    (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkoxy]carbonyloxy,     -    (C₅-C₆)-cycloalkenyl-[(C₁-C₄)-alkoxy]carbonyloxy,     -    (C₅-C₆)-cycloalkynyl-[(C₁-C₄)-alkoxy]carbonyloxy,     -    (C₃-C₆)-cycloalkoxycarbonyloxy,     -    (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkyl]carbonyloxy,     -    (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkoxy]carbonyloxy,     -    (C₃-C₆)-cycloalkylcarbonylamino,     -    (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkyl]carbonylamino,     -    (C₅-C₆)-cycloalkenyl-[(C₁-C₄)-alkyl]carbonylamino,     -    (C₅-C₆)-cycloalkynyl-[(C₁-C₄)-alkyl]carbonylamino,     -    (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkoxy]carbonylamino,     -    (C₃-C₆)-cycloalkoxycarbonylamino,     -    (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkyl]carbonylamino and     -    (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkoxy]carbonylamino,     -    phenylcarbonyl,     -    phenyl-[(C₁-C₄)-alkyl]carbonyl,     -    phenyl-[(C₁-C₄)-alkoxy]carbonyl,     -    phenoxycarbonyl,     -    phenoxy-[(C₁-C₄)-alkyl]carbonyl,     -    phenoxy-[(C₁-C₄)-alkoxy]carbonyl,     -    phenylcarbonyloxy,     -    phenyl-[(C₁-C₄)-alkyl]carbonyloxy,     -    phenyl-[(C₁-C₄)-alkoxy]carbonyloxy,     -    phenoxycarbonyloxy,     -    phenoxy-[(C₁-C₄)-alkyl]carbonyloxy,     -    phenoxy-[(C₁-C₄)-alkoxy]carbonyloxy,     -    phenylcarbonylamino,     -    phenyl-[(C₁-C₄)-alkyl]carbonylamino,     -    phenyl-[(C₁-C₄)-alkoxy]carbonylamino,     -    phenoxycarbonylamino,     -    phenoxy-[(C₁-C₄)-alkyl]carbonylamino,     -    phenoxy-[(C₁-C₄)-alkoxy]carbonylamino,     -    where each of the 42 last-mentioned radicals is optionally         fused in the cyclic moiety with a carbocyclic or heterocyclic         ring, preferably a carbocyclic ring having 3 to 6 carbon atoms         or a heterocyclic ring having 5 or 6 ring atoms and 1 to 3 ring         heteroatoms from the group consisting of N, O and S, preferably         benzo-fused, and unsubstituted at the ring or at the polycyclic         system or substituted by one or more radicals from the group         consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy,         (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy and nitro, and     -   (c′) radicals of the formulae —SiR′₃, —O—SiR′₃,         (R′)₃Si—(C₁-C₆)-alkoxy, —CO—O—NR′₂, —O—N═CR′₂, —N═CR′₂, —O—NR′₂,         —CH(OR′)₂ and —O—(CH₂)_(q)—CH(OH)₂, in which each of the         radicals R′ independently of the others represents H,         (C₁-C₄)-alkyl or phenyl, which is unsubstituted or substituted         by one or more radicals from the group consisting of halogen,         (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,         (C₁-C₄)-haloalkoxy and nitro or at two adjacent positions by a         (C₂-C₆)-alkylene bridge, and q represents an integer from 0 to         6, and     -   (d′) radicals of the formula R″O—CHR′″CH(OR″)—(C₁-C₆)-alkoxy, in         which each of the radicals R″ independently of the others is H         or (C₁-C₄)-alkyl or together the radicals are a (C₁-C₆)-alkylene         group and R′″ is H or (C₁-C₄)-alkyl, and     -   (e′) a radical of the formula Het⁷ which is unsubstituted or         substituted by one or more identical or different radicals         R^(B),     -   or -   R⁴ represents a polycyclic radical based on (C₃-C₆)-cycloalkyl,     (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkynyl or phenyl, where the base     ring is fused with a carbocyclic or heterocyclic ring, preferably a     5- or 6-membered ring having 0 or 1 to 3 ring heteroatoms from the     group consisting of N, O and S, preferably benzo-fused, and where     the base ring or the polycyclic system is unsubstituted or     substituted by one or more identical or different radicals R^(B),     preferably unsubstituted or substituted by one or more radicals from     the group consisting of halogen, cyano, nitro, hydroxy, carboxy,     (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,     (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl,     (C₂-C₄)-haloalkynyl, (C₁-C₄)-alkoxy, (C₂-C₄)-alkenyloxy,     (C₂-C₄)-alkynyloxy, (C₁-C₄)-haloalkoxy,     (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio,     (C₂-C₄)-alkenylthio, (C₂-C₄)-alkynylthio, (C₃-C₆)-cycloalkyl,     (C₃-C₆)-cycloalkoxy, [(C₁-C₄)-alkoxy]carbonyl,     [(C₁-C₄)-haloalkoxy]carbonyl and oxo, -    or -   R⁴ represents a heterocyclic radical Het⁷ which is unsubstituted in     the ring or in the polycyclic system or substituted by one or more     identical or different radicals R^(B), preferably unsubstituted or     substituted by one or more radicals from the group consisting of     halogen, cyano, thio, nitro, hydroxy, carboxy, (C₁-C₄)-alkyl,     (C₁-C6)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl,     (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl,     (C₁-C₆)-alkoxy, (C₂-C₄)-alkenyloxy, (C₂-C₄)-alkynyloxy,     (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,     (C₁-C₄)-alkylthio, (C₂-C₄)-alkenylthio, (C₂-C₄)-alkynylthio,     (C₃-C₄)-cycloalkyl, (C₃-C₆)-cycloalkoxy, [(C₁-C₄)-alkoxy]carbonyl,     [(C₁-C₆)-haloalkoxy]carbonyl and oxo,     where Het⁷, R*, R**, R^(A), R^(B), R^(C), R^(D), R^(aa), R^(bb) and     R^(cc) have the meanings already mentioned above, preferably -   Het⁷ in each case independently of the others is a saturated,     partially unsaturated or heteroaromatic monocyclic heterocyclyl     radical having 3 to 9 ring atoms, preferably having 5 or 6 ring     atoms, or a 9- or 10-membered bicyclic heterocycle which contains 1,     2, 3 or 4 heteroatoms selected from the group consisting of O, N and     S, preferably a 5- or 6-membered heterocycle having 1 to 3 ring     heteroatoms from the group consisting of N, O and S which is     optionally also fused to a carbocyclic or heterocyclic ring,     preferably a carbocyclic ring having 3 to 6 carbon atoms or a     heterocyclic ring having 5 or 6 ring atoms and 1 to 3 ring     heteroatoms from the group consisting of N, O and S, preferably     optionally benzo-fused, -   R*, R** independently of one another (i.e. also of other groups     NR*R**) each represent H, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,     (C₂-C₆)-alkynyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-alkanoyl,     [(C₁-C₄)-haloalkyl]carbonyl, [(C₁-C₄)-alkoxy]carbonyl,     [(C₁-C₄)-haloalkoxy]carbonyl, (C₃-C₆)-cycloalkyl,     (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl, phenyl, phenyl-(C₁-C₄)-alkyl,     where each of the 4 last-mentioned radicals is optionally     substituted in the cycle by one or more identical or different     radicals R^(bb), or preferably     -    H, (C₁-C₄)-alkyl, allyl, propargyl,         (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, formyl, acetyl, n-propanoyl,         isopropanoyl, trifluoroacetyl, trichloroacetyl, methoxycarbonyl,         ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, sec-,         t-Butoxycarbonyl, [(C₁-C₄)-haloalkoxy]-carbonyl, cyclopropyl,         cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, phenyl,         benzyl, 1- or 2-phenylethyl, -   R* and R** together with the nitrogen atom represent a preferably     saturated 5- to 6-membered heterocycle which, in addition to the     nitrogen atom, may contain one or two further ring heteroatoms from     the group consisting of N, O and S and which may be unsubstituted or     substituted by one or more radicals from the group consisting of     (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo, preferably a 1-piperidine,     1-piperazine, 1-pyrrolidine, 1-pyrazolidine, 1-piperazolidine or     1-morpholine radical, -   R^(A) represents halogen, cyano, hydroxy or (C₁-C₆)-alkoxy, -   R^(B) represents halogen, cyano, hydroxy, oxo, nitro, (C₁-C₄)-alkyl,     (C₁-C₄)-haloalkyl, cyano-(C₁-C₄)-alkyl, hydroxy-(C₁-C₄)-alkyl,     nitro-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl,     (C₁-C₄)-alkoxy, (C₂-C₄)-alkenyloxy, (C₂-C₄)-alkynyloxy,     (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,     (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio,     (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-haloalkylsulphonyl, a radical of the     formula R^(aa)—C(═O)— or R^(aa)—C(═O)—(C₁-C₆)-alkyl, where the     radicals R^(aa) are defined below, —NR*R**, where R* and R** are     defined below, cyclopropyl, cyclopropylmethyl, phenyl, benzyl, 1- or     2-phenylethyl, phenoxy, 2-phenoxyethyl or a 5- or 6-membered     monocyclic or 9- or 10-membered bicyclic heterocycle which contains     1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N     and S, where each of the 9 last-mentioned radicals is optionally     substituted in the cyclic moiety by one or more identical or     different radicals R^(bb), -   R^(C), R^(D) are each independently of one another (also     independently of radicals R^(C), R^(D) in other groups) -    hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,     -   where each of the 3 last-mentioned radicals is unsubstituted or         substituted by one or more radicals from the group consisting of         halogen, cyano, nitro, hydroxy, (C₁-C₄)-alkoxy,         (C₂-C₄)-alkenyloxy, (C₂-C₄)-alkynyloxy, (C₁-C₄)-haloalkoxy,         (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio,         (C₁-C₆)-alkylsulphonyl and (C₁-C₈)-haloalkylsulphonyl, -    or -    (C₃-C₆)-cycloalkyl, (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkynyl,     phenyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl-(C₁-C₄)-alkyl,     phenoxy-(C₁-C₄)-alkyl or phenylamino-(C₁-C₆)-alkyl, radicals Het⁷,     Het⁷-(C₁-C₆)-alkyl, Het⁷-O—(C₁-C₆)-Alkyl, where Het⁷ has the meaning     mentioned,     -   where each of the 12 last-mentioned radicals is unsubstituted in         the acyclic moiety or substituted by one or more identical or         different radicals R^(A) and is unsubstituted in the cyclic         moiety or substituted by one or more identical or different         radicals R^(B), -   R^(aa) independently of one another each represent hydrogen, OH,     (C₁-C₆)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl,     (C₁-C₆)-alkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,     (C₁-C₄)-alkoxy-(C₁-C₄)-alkyloxy, (C₁-C₄)-haloalkoxy,     (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkoxy,     —NR*R*, where R* and R** are as defined above, (C₃-C₆)-cycloalkyl,     (C₃-C₆)-cycloalkoxy, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,     (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkoxy, phenyl, phenyl-(C₁-C₄)-alkyl,     phenyl-(C₁-C₄)-alkoxy, phenoxy, phenoxy-(C₁-C₄)-alkyl,     phenoxy-(C₁-C₄)-alkoxy, phenylamino, phenylamino-(C₁-C₄)-alkyl,     phenylamino-(C₁-C₄)-alkoxy or 5- or 6-membered monocyclic or 9- or     10-membered bicyclic heterocycle which is optionally attached via a     (C₁-C₄)-alkylene group or a (C₁-C₄)-alkoxy group and contains 1, 2,     3 or 4 heteroatoms selected from the group consisting of O, N and S,     where each of the 14 last-mentioned radicals is optionally     substituted in the cyclic moiety by one or more identical or     different radicals R^(cc), -   R^(bb) independently of one another each represent halogen,     (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy or     (C₁-C₄)-haloalkoxy, preferably halogen, methyl, CF₃, CCl₃, methoxy,     ethoxy, OCH₂F, OCF₂H or OCF₃ and -   R^(cc) independently of one another each represent halogen,     (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy or     (C₁-C₄)-haloalkoxy, preferably halogen, methyl, CF₃, CCl₃, methoxy,     ethoxy, OCH₂F, OCF₂H or OCF₃.

More preference is here also given to compounds (I), preferably of the formula (Ia), or salts thereof in which

-   R⁴ represents H, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, -    where each of the 3 last-mentioned radicals is unsubstituted or     substituted by one or more radicals from the group consisting of     halogen, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, alkylsulphinyl,     alkylsulphonyl, (C₃-C₆)-cycloalkyl which is unsubstituted or     substituted by one or more radicals from the group consisting of     halogen and (C₁-C₄)-alkyl, and -    phenyl, phenoxy, phenylthio, phenylsulphinyl, phenylsulphonyl,     where the phenyl ring in the 5 last-mentioned radicals is in each     case unsubstituted or substituted by one or more radicals from the     group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and     (C₁-C₄)-haloalkyl, and -    a radical Het⁷, preferably a saturated or partially unsaturated     monocyclic heterocyclyl radical which has 5 or 6 ring atoms and     contains 1, 2 or 3 heteroatoms selected from the group consisting of     O, N and S and is unsubstituted or substituted by one or more     radicals selected from the group consisting of halogen,     (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkyl, -    or -   R⁴ represents (C₃-C₆)-cycloalkyl which is unsubstituted or     substituted by one or more radials from the group consisting of     (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkyl, -    or -   R⁴ represents phenyl which is unsubstituted or substituted by one or     more radials from the group consisting of halogen, (C₁-C₄)-alkyl,     (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkyl.

Particular preference is here also given to compounds (I), preferably of the formula (Ia), or salts thereof in which

-   R⁴ represents H, (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl or (C₂-C₄)-alkynyl, -    where each of the 3 last-mentioned radicals is unsubstituted or     substituted by one or more radicals from the group consisting of     halogen, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, cyclopropyl, cyclobutyl,     where each of the two last-mentioned radicals is unsubstituted or     substituted by one or more radicals from the group consisting of     halogen and (C₁-C₄)-alkyl, and phenyl, phenylthio     (=phenylsulphanyl), phenylsulphinyl, phenylsulphonyl, where each of     the 4 last-mentioned radicals is unsubstituted or substituted by one     or more radicals from the group consisting of halogen,     (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkyl.

More preferably

-   R⁴ also represents a polycyclic radical based on (C₃-C₉)-cycloalkyl,     (C₅-C₉)-cycloalkenyl, (C₅-C₉)-cycloalkynyl or phenyl, where the base     ring is condensed, preferably benzo-fused, with a carbocyclic or     heterocyclic ring, preferably a 5- or 6-membered ring having 0 or 1     to 3 ring heteroatoms from the group consisting of N, O and S, and     where the base ring or the polycyclic system is unsubstituted or     substituted by one or more radicals from the group consisting of     halogen, cyano, nitro, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,     (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl,     (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,     (C₁-C₄)-alkylthio, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkoxy,     [(C₁-C₄)-alkoxy]carbonyl and [(C₁-C₄)-haloalkoxy]carbonyl.

Preference is also given to compounds (I), preferably of the formula (Ia), or salts thereof in which

-   R⁴ represents a saturated, partially unsaturated or heteroaromatic     heterocyclyl radical which has 3 to 9 ring atoms, preferably 5 or 6     ring atoms, which has 1 to 4 heteroatoms, preferably 1 to 3 ring     heteroatoms from the group consisting of N, O and S and which is     unsubstituted or substituted by one or more identical or different     radicals from the group consisting of halogen, cyano, thio, nitro,     hydroxy, (C1-C₆)-alkyl, (C₁-C6)-haloalkyl,     (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₆)-haloalkenyl,     (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₁-C₆)-alkoxy,     (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkoxy,     (C₁-C₆)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio,     (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₃-C₆)-cycloalkyl,     (C₃-C₆)-cycloalkoxy, [(C₁-C₈)-alkoxy]carbonyl,     [(C₁-C₆)-haloalkoxy]carbonyl and oxo.

Preference is also given to compounds (I), preferably of the formula (Ia), or salts thereof in which

-   R⁴ represents a radical of the formula SiR^(a)R^(b)R^(c),     —NR^(a)R^(b) or —N═CR^(c)R^(d), preferably of the formula     —NR^(a)R^(b) or —N═CR^(c)R^(d), -    where in the 5 last-mentioned formulae each of the radicals R^(a),     R^(b), R^(c) and R^(d) independently of the others represents     hydrogen, (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, benzyl,     substituted benzyl, phenyl or substituted phenyl, but where SiH₃ for     SiR^(a)R^(b)R^(c) is excluded, or R^(a) and R^(b) together with the     nitrogen atom represent a 3- to 8-membered heterocycle which, in     addition to the nitrogen atom, may contain one or two further ring     heteroatoms from the group consisting of N, O and S and which is     unsubstituted or substituted by one or more radicals from the group     consisting of (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl, or R^(c) and     R^(d) together with the carbon atom represent a 3- to 8-membered     carbocyclic radical or heterocyclic radical which may contain 1 to 3     ring heteroatoms from the group consisting of N, O and S, where the     carbocyclic or heterocyclic radical is unsubstituted or substituted     by one or more radicals from the group consisting of (C₁-C₄)-alkyl     and (C₁-C₄)-haloalkyl.

Particular preference is also given to compounds (I), preferably of the formula (Ia), or salts thereof in which

-   R⁴ represents H, methyl, ethyl, n-propyl, i-propyl, n-butyl,     s-butyl, i-butyl, t-butyl, allyl, ethynyl, propargyl     (prop-2-yn-1-yl), prop-1-yn-1-yl, but-2-yn-1-yl, but-3-yn-1-yl,     2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl,     3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl,     methylprop-2-yn-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl,     but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl,     3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl,     1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or     (Z)-pent-3-en-2-yl, -    phenyl, 2-carboxyphenyl, 2-chlorophenyl, 3-chlorophenyl,     4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl,     3-methoxyphenyl, 4-methoxyphenyl, 2-methoxyphenyl, 3-methoxyphenyl,     4-methoxyphenyl, benzyl, 2-fluorobenzyl, 2-fluorobenzyl,     3-fluorobenzyl, 4-fluorobenzyl, 2,3-difluorobenzyl,     2,4-difluorobenzyl, 2,5-difluorobenzyl, 2,6-difluorobenzyl,     3,4-difluorobenzyl, 3,5-difluorobenzyl, 2-phenylethyl,     1-phenylethyl, (4-chlorophenyl)methyl [i.e.     ═CH₂(4-Cl-Ph)=4-chlorobenzyl], (4-fluorophenyl)methyl [d. h.     ═CH₂(4-F-Ph)], (4-methoxyphenyl)methyl [i.e. ═CH₂(4-OMe-Ph)],     2-phenoxyethyl, 2-phenylthioethyl [=2-(phenylsulphanyl)ethyl],     2-phenylsulphinylethyl, 2-phenylsulphonylethyl, trifluoromethyl,     difluoromethyl, fluoromethyl, trichloromethyl, dichloromethyl,     chloromethyl, -    methoxymethyl, 2-methoxyethyl, 2,2,2-trifluoroethyl,     1,1,1-trifluoroprop-2-yl, 2,2-difluoroethyl, 1,3-difluoroprop-2-yl,     2,3-dimethoxypropyl, 2,3-dimethoxyprop-2-yl, 2,2-dimethoxyeth-2-yl,     2-(2,2,2-trifluoroethoxy)ethyl, 2-fluoroethyl, 2-chloroethyl,     2-bromoethyl, 2-iodoethyl, 2,2,3,3,3-pentafluoropropyl,     1-hydroxyprop-2-yl, 2-hydroxyprop-2-yl, 2-hydroxyprop-1-yl,     3-hydroxypropyl, 3-hydroxyprop-2-yl, -    (2-methoxyethoxy)methyl; 2-(2-methoxyethoxy)ethyl;     (2-ethoxyethoxy)methyl; 2-(2-ethoxyethoxy)ethyl, -    (acetoxy)methyl, (propanoyloxy)methyl,     (2-methylpropanoyloxy)methyl, (2,2-dimethylpropanoyloxy)methyl,     1-(acetoxy)ethyl, 2-(acetoxy)ethyl, 2-(propanoyloxy)ethyl,     1-(propanoyloxy)ethyl, 1-(2-methylpropanoyloxy)eth-1-yl,     2-(2-methylpropanoyloxy)eth-1-yl, 2-(2,2-dimethylpropanoyloxy)ethyl     [i.e. 1-(t-butylcarbonyloxy)ethyl],     2-(2,2-dimethylpropanoyloxy)ethyl; -    1-(2,2-dimethylpropanoyloxy)-2-methylprop-1-yl,     1-(t-butylcarbonyloxy)-2-methylprop-1-yl, -    (methoxycarbonyl)methyl, (ethoxycarbonyl)methyl,     (n-propoxycarbonyl)methyl, (1-propoxycarbonyl)methyl,     (n-butoxycarbonyl)methyl, (s-butoxycarbonyl)methyl,     (1-butoxycarbonyl)methyl, (t-butoxycarbonyl)methyl,     1-(methoxycarbonyl)ethyl, 2-(methoxycarbonyl)ethyl,     1-(ethoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl,     1-(n-propoxycarbonyl)ethyl, 2-(n-propoxycarbonyl)ethyl,     1-(1-propoxycarbonyl)ethyl, 2-(1-propoxycarbonyl)ethyl,     1-(n-butoxycarbonyl)ethyl, 2-(n-butoxycarbonyl)ethyl,     1-(s-butoxycarbonyl)ethyl, 2-(s-butoxycarbonyl)ethyl,     1-(1-butoxycarbonyl)ethyl, 2-(1-butoxycarbonyl)ethyl,     1-(t-butoxycarbonyl)ethyl, 2-(t-butoxycarbonyl)ethyl, -    (methoxycarbonyloxy)methyl, (ethoxycarbonyloxy)methyl,     (n-propoxycarbonyloxy)methyl, (1-propoxycarbonyloxy)methyl,     (n-butoxycarbonyloxy)methyl, (s-butoxycarbonyloxy)methyl,     (1-butoxycarbonyloxy)methyl, (t-butoxycarbonyloxy)methyl,     1-(methoxycarbonyloxy)ethyl, 2-(methoxycarbonyloxy)ethyl,     1-(ethoxycarbonyloxy)ethyl, 2-(ethoxycarbonyloxy)ethyl,     1-(n-propoxycarbonyloxy)ethyl, 2-(n-propoxycarbonyloxy)ethyl,     1-(1-propoxycarbonyloxy)ethyl, 2-(1-propoxycarbonyloxy)ethyl,     1-(n-butoxycarbonyloxy)ethyl, 2-(n-butoxycarbonyloxy)ethyl,     1-(s-butoxycarbonyloxy)ethyl, 2-(s-butoxycarbonyloxy)ethyl,     1-(1-butoxycarbonyloxy)ethyl, 2-(1-butoxycarbonyloxy)ethyl,     1-(t-butoxycarbonyloxy)ethyl, 2-(t-butoxycarbonyloxy)ethyl,     (cyclohexoxycarbonyloxy)methyl, 1-(cyclohexoxycarbonyloxy)eth-1-yl,     2-(cyclohexoxycarbonyloxy)eth-1-yl, -    (acetyl)methyl, 1-(acetyl)ethyl, 2-(acetyl)ethyl, 1-(acetyl)propyl,     2-(acetyl)propyl, 3-(acetyl)propyl, (propanoyl)methyl,     1-(propanoyl)ethyl, 2-(propanoyl)ethyl, 1-(propanoyl)propyl,     2-(propanoyl)propyl, 3-(propanoyl)propyl,     1-(propanoyl)-2-methylpropyl, -    2-ethylthioethyl [=2-(ethylsulphanyl)ethyl],     2-(ethylsulphinyl)ethyl, 2-(ethylsulphonyl)ethyl, -    2-(ethylideneaminooxy)ethyl, 2-(prop-2-ylideneaminooxy)ethyl,     2-(but-2-ylideneaminooxy)ethyl, 2-(pent-3-ylideneaminooxy)ethyl, -   (N,N-dimethylamino)methyl, 2-(N,N-dimethylamino)eth-1-yl,     1-(N,N-dimethylamino)eth-1-yl, 2-(N,N-diethylamino)eth-1-yl,     1-(N,N-diethylamino)eth-1-yl, (N,N-diethylamino)methyl, -    (N,N-dimethylaminocarbonyl)methyl,     1-(N,N-dimethylaminocarbonyl)ethyl,     2-(N,N-dimethylaminocarbonyl)ethyl,     (N,N-diethylaminocarbonyl)methyl, 1-(N,N-diethylaminocarbonyl)ethyl,     2-(N,N-diethylaminocarbonyl)ethyl, 1-(dimethylamino)prop-2-yl [i.e.     2-(dimethylamino)-1-methylethyl], 1-(diethylamino)prop-2-yl, -    trimethylsilylmethyl, 1-(trimethylsilyl)ethyl,     2-(trimethylsilyl)ethyl, triethylsilylmethyl,     1-(triethylsilyl)ethyl, 2-(triethylsilyl)ethyl, -    cyclopropyl, cyclopropylmethyl, 1-cyclopropylethyl,     2-cyclopropylethyl, (1-methylcyclopropyl)methyl,     1-(1-methylcyclopropyl)ethyl, 2-(1-methylcyclopropyl)ethyl,     (2,2-dichlorcyclopropyl)methyl, 1-(2,2-dichlorcyclopropyl)ethyl,     2-(2,2-dichlorcyclopropyl)ethyl, (2,2-dimethylcyclopropyl)methyl,     1-(2,2-dimethylcyclopropyl)ethyl, 2-(2,2-dimethylcyclopropyl)ethyl,     cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl or -    pyrid-2-yl, pyrid-3-yl, pyrid-4-yl, 2-chloropyrid-3-yl,     3-chloropyrid-2-yl, thien-2-yl, thien-3-yl, 2-chlorothien-3-yl,     3-chlorothien-2-yl, 4-chlorothien-2-yl, thietan-3-yl, -    (1-ethyl-5-methyl-1H-pyrazol-4-yl)methyl,     1-(1-ethyl-5-methyl-1H-pyrazol-4-yl)ethyl,     2-(1-ethyl-5-methyl-1H-pyrazol-4-yl)ethyl, -    (1-ethyl-3-methyl-1H-pyrazol-4-yl)methyl,     1-(1-ethyl-3-methyl-1H-pyrazol-4-yl)ethyl,     2-(1-ethyl-3-methyl-1H-pyrazol-4-yl)ethyl, -    tetrahydrofuran-2-yl, tetrahydrofuran-3-yl,     tetrahydrofuran-2-ylmethyl, tetrahydrofuran-3-ylmethyl,     (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl; -    oxetan-3-yl, (oxetan-3-yl)methyl, (oxetan-2-yl)methyl,     (1,3-dioxolan-2-yl)methyl, (1,3-dioxolan-4-yl)methyl,     5-methyl-2-oxo-1,3-dioxolan-4-yl)methyl, (morpholin-4-yl)methyl;     1-(morpholin-4-yl)ethyl, 2-(morpholin-4-yl)ethyl,     2,3-dihydro-1H-inden-2-yl, dihydro-1H-inden-3-yl,     dihydro-1H-inden-4-yl, dihydro-1H-inden-5-yl, 1H-inden-2-yl,     1H-inden-3-yl, 1H-inden-4-yl, 1H-inden-5-yl, 1H-inden-6-yl or     1H-inden-7-yl.

Here, very particular preference is given to compounds (I), preferably of the formula (Ia), and salts thereof in which

-   R⁴ represents H, methyl, ethyl, n-propyl, isopropyl, n-butyl,     s-butyl, isobutyl, t-butyl, phenyl, benzyl, CH₂(4-Cl-Ph), i.e.     (4-chlorophenyl)methyl, CH₂(4-F-Ph), i.e. (4-fluorophenyl)methyl,     CH₂(4-OMe-Ph), i.e. (4-methoxyphenyl)methyl, 2-fluorobenzyl,     2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2,3-difluorobenzyl,     2,4-difluorobenzyl, 2,5-difluorobenzyl, 2,6-difluorobenzyl,     3,4-difluorobenzyl, 3,5-difluorobenzyl, 2-phenoxyethyl,     2-ethylthioethyl, 2-ethylsulphinylethyl, 2-ethylsulphonylethyl,     2-phenylthioethyl, 2-phenylsulphinylethyl, 2-phenylsulphonylethyl,     methoxymethyl, 2-methoxyethyl, tetrahydrofuran-2-ylmethyl,     2-(dimethylamino)ethyl, oxetan-3-yl, (3-methyloxetan-3-yl)methyl,     thietan-3-yl, trifluoromethyl, difluoromethyl, 2,2,2-trifluoroethyl,     2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl,     cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl,     (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl,     tetrahydrofuran-2-ylmethyl, allyl, ethynyl, propargyl     (=prop-2-yn-1-yl), prop-1-yn-1-yl, 2-chloroprop-2-en-1-yl,     3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl,     3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl,     2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl,     but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl,     3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl,     (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl,     cyclopentylmethyl, cyclohexylmethyl or     1-ethyl-5-methyl-1H-pyrazol-4-methyl, i.e.     (1-ethyl-5-methyl-1H-pyrazol-4-yl)methyl.

Here, very particular preference is given to compounds (I), preferably of the formula (Ia), and salts thereof in which

-   R⁴ represents H, methyl, ethyl, n-butyl, s-butyl, isobutyl, t-butyl,     allyl and propargyl, in particular methyl or ethyl.

The invention also includes all tautomers, such as keto and enol tautomers, and their mixtures and salts, if appropriate functional groups are present.

The present invention also provides processes for preparing the compounds of the general formula (I) or (Ia) and/or their salts. This includes processes which can be carried out analogously to known methods.

To prepare the compounds (I) according to the invention, it is possible to use initially the corresponding diastereomer mixtures in the form of their racemic mixtures. The preparation of the diastereomer mixtures of the cyanobutyrates is known in principle; see, for example, EP-A 5341, EP-A 266725, EP-A270 830, JP 04/297454, JP 04/297455, JP 05/058979, WO 2011/003776, WO 2011/003775, WO 2011/042378, WO 2011/073143, WO 2011/098417.

Analogously to the synthesis routes described in the publications cited, the compounds can be prepared by standard processes of organic chemistry.

Diastereomer mixtures of the compounds of the formula (I) comprising the compound (I) to be prepared are obtained, for example, characterized in that (a) compounds of the formula (II) (“cyanomethylpyridines”/“pyridylacetonitriles”)

-    are reacted with compounds of the formula (III) (cinnamic acid     derivatives) or salts thereof

-    to give compounds of the formula (I) (diastereomers/racemic)

-    where R¹, R², R³, R⁴, m and n in the compounds (II) and (III) are     as defined in the respective compound of the formula (I) to be     prepared.

In the process mentioned above and in the processes below, in some cases solvents are employed. In this context, “inert solvents” refers in each case to solvents which are inert under the particular reaction conditions, but which do not have to be inert under all reaction conditions.

The process described in each case can be carried out in apparatuses customary in the laboratory, in pilot plants and in plants for preparing commercial amounts and industrial processes, or alternatively also in a microwave oven.

The starting materials (III) required for preparing the compounds (I) are known from the literature cited above or can be prepared analogously to the literature cited.

The starting materials (II) required for preparing the compounds (I) are commercially available, described in the literature or can be prepared analogously to processes described in the literature.

The reaction according to variant (a) can be carried out, for example, according to methods and under conditions like those known for Michael additions. The reaction is carried out, for example, at temperatures of from −100° C. to 150° C., preferably from −78° C. to 100° C., in an organic or inorganic solvent, generally in the presence of a base or a catalyst or both [cf. J. Chem. Soc. (1945), p. 438].

Suitable solvents are, for example, organic solvents such as:

-   -   aliphatic hydrocarbons such as pentane, hexane, cyclohexane or         petroleum ether;     -   aromatic hydrocarbons such as toluene, o-, m- or p-xylene,     -   halogenated hydrocarbons such as methylene chloride, chloroform         or chlorobenzene,     -   ethers, such as diethyl ether, diisopropyl ether, tert-butyl         methyl ether, dioxane, anisole and tetrahydrofuran (THF),     -   nitriles such as acetonitrile or propionitrile,     -   ketones such as acetone, methyl ethyl ketone, diethyl ketone and         tert-butyl methyl ketone,     -   alcohols such as methanol, ethanol, n-propanol, isopropanol,         n-butanol and tert-butanol, and also     -   dimethyl sulphoxide, dimethylformamide, dimethylacetamide,         sulpholane,     -   mixtures of the organic solvents mentioned.

In individual cases, it is also appropriate to use inorganic solvents such as water or mixtures of organic solvents with water.

Preferred solvents are THF, toluene and methanol, and mixtures thereof with other organic solvents.

The reaction by preparation variant (a) is preferably carried out in the presence of a base, for example from the group consisting of the inorganic compounds such as the alkali metal and alkaline earth metal hydroxides, for example lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, the alkali metal and alkaline earth metal oxides, for example lithium oxide, sodium oxide, calcium oxide or magnesium oxide, the alkali metal and alkaline earth metal hydrides, for example lithium hydride, sodium hydride, potassium hydride or calcium hydride, the alkali metal amides, for example lithium amide, sodium amide or potassium amide, the alkali metal and alkaline earth metal carbonates, for example lithium carbonate, potassium carbonate or calcium carbonate, the alkali metal bicarbonates, for example sodium bicarbonate, or the organometallic compounds such as, preferably, the alkali metal alkyls, for example methyllithium, butyllithium or phenyllithium, the alkylmagnesium halides, for example methylmagnesium chloride, or the alkali metal and alkaline earth metal alkoxides, for example sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide or dimethoxymagnesium.

The bases used can also be organic bases, for example from the group consisting of the tertiary aliphatic amines, for example trimethylamine, triethylamine, tributylamine, diisopropylethylamine or N-methylpiperidine, or the aromatic tertiary amines, for example pyridine or substituted pyridines such as collidine, lutidine or 4-dimethylaminopyridine, or the bicyclic amines such as 7-methyl-1,5,7-triazabicyclo[4.4.0]-dec-5-ene or 1,8-diazabicyclo[5.4.0]undec-7ene (DBU). Preferred bases are, for example, potassium tert-butoxide, lithium bis(trimethylsilyl)amide, DBU or 7-methyl-1,5,7-triazabicyclo[4.4.0]-dec-5-ene.

The amount of base may generally be varied within wide limits. For example, it may be expedient to employ the base in catalytic amounts, in substoichiometric amounts, in equimolar amounts or in excess. A preferably liquid organic base may optionally also be used as solvent.

Suitable catalysts for the Michael addition according to variant (a) are acidic catalysts, for example from the group consisting of the inorganic acids, for example Broensted acids, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulphuric acid or perchloric acid, or Lewis acids, such as boron trifluoride, aluminium trichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride, scandium(III) triflate or zinc(II) chloride, and also organic acids, for example formic acid, acetic acid, propionic acid, oxalic acid, toluenesulphonic acid, benzenesulphonic acid, camphorsulphonic acid, citric acid or trifluoroacetic acid.

The amount of acidic catalyst may generally be varied within wide limits. For example, it may be expedient to employ the acid in catalytic amounts, in substoichiometric amounts, in equimolar amounts or in excess. A preferably liquid acid may optionally also be used as solvent.

Variant (a1) for the preparation of intermediates of the formula (II):

Compounds of the formula (II) and salts thereof in which R¹, R³ and m are defined as in the respective compound of the formula (I) to be prepared are also obtained, for example, according to process [variant (a1)], characterized in that a pyridinecarboxylic acid of the formula (IV) or its ester of the formula (V),

where the radical R in the formula (V) represents a hydrocarbon radical, preferably (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl or (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, in particular methyl or ethyl, is reduced to give the compound of the formula (VI) (=reduction at the acid or ester group),

and the compound (VI) is converted into the compound (VII),

where X represents a leaving group, for example halogen, such as chlorine, bromine or iodine, obtained by a halogenation reaction such as, for example, substitution by halide, or sulphonates of the formula —O—SO₂—R(R═(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, phenyl, which is optionally substituted, for example by halogen, nitro or alkyl), for example mesylate (R=methyl), triflate (R=CF₃), tosylate (R=p-tolyl), bromylate (R=p-bromophenyl), nosylate (R=p-nitrophenyl), obtained by esterification of an appropriate sulphonyl chloride with compounds of the formula (VI), and the compound (VII) is converted by substitution with cyanide into the compound (II),

where R¹, R³ and m in the formulae (IV), (V), (VI) and (VII) are as defined in formula (II) or formula (I).

The individual synthesis steps according to variant (a1) are known in principle to the person skilled in the art and described, for example, in Acta Pharm. Suecica 1972, 9, 411-418; J. Org. Chem. 1999, 64 (23), 8576-8581; Synthesis 1998, 9, 1335-1338; J. Med. Chem. 2000, 43 (18) 3386-3399; U.S. Pat. No. 5,225,423 (Shell Research Limited 1993), U.S. Pat. No. 4,966,902 (Hoechst AG, 1990); WO2007/045989 (Pfizer Limited, 2007); US2004/242572 (Boehringer Ingelheim International GmbH, 2004) and the literature cited therein.

Diastereomer mixtures or racemic diastereomers of the compounds of the formula (I) can be obtained according to variant (b) by transesterification, characterized in that

-   (b) compounds of the formula (I*)

-    in which R is a radical from the group consisting of the radicals     possible for R⁴′ but different from the radical R⁴ in the     compound (I) to be prepared, is reacted with a compound of the     formula R⁴—OH in which R⁴ is defined as in formula (I), to give     compound (I), where R¹, R², R³, m and n in the compound (I*) are as     defined in the compound of the formula (I) to be prepared in each     case.

In a particular embodiment, according to variant (b1) it is also possible to obtain, as compounds (I), stereochemically enriched compounds of the formula (Ia), characterized in that (b1) stereochemically enriched compounds of the formula (Ia*), which correspond stereochemically [i.e. are at least as enriched as in the desired compound (Ia)]

-   in which R is a radical from the group consisting of the radicals     possible for R⁴, but different from the radical R⁴ in the compound     (Ia) to be prepared, is reacted with a compound of the formula R⁴—OH     in which R⁴ is defined as in the compound of the formula (Ia) to be     prepared.

The transesterifications (b) and (b1) can be carried out, for example, using a suitable alcohol R⁴—OH in the presence of a catalyst, optionally in the presence of an aprotic solvent. Furthermore, in general, those conditions are advantageous where the chemical equilibrium is shifted to the side of the desired product, for example using a large excess of the alcohol R⁴—OH under virtually anhydrous conditions, for example in the presence of a molecular sieve.

The reactions (transesterifications) can generally be carried out at temperatures of from 0° C. to 180° C., preferably from 20° C. to 100° C., in the presence of a Lewis or Broenstedt acid or an enzyme [cf. J. Org. Chem. 2002, 67, 431].

Suitable solvents are, for example, organic aprotic solvents such as:

-   -   aliphatic hydrocarbons such as pentane, hexane, cyclohexane or         petroleum ether;     -   aromatic hydrocarbons such as toluene, o-, m- or p-xylene,     -   halogenated hydrocarbons such as methylene chloride         (dichloromethane), chloroform or chlorobenzene,     -   ethers, such as diethyl ether, diisopropyl ether, tert-butyl         methyl ether, dioxane, anisole or tetrahydrofuran (THF),     -   nitriles such as acetonitrile or propionitrile,     -   ketones such as acetone, methyl ethyl ketone, diethyl ketone and         tert-butyl methyl ketone,     -   dimethyl sulphoxide, dimethylformamide, dimethylacetamide or         sulpholane or     -   mixtures of the organic solvents mentioned.

The preferred solvent is the alcohol R⁴—OH, which is at the same time used as reaction partner for the transesterification, optionally in combination with one of the aprotic organic solvents mentioned.

Alternatively, it is also possible to obtain the desired ester from another ester in two steps by acidic or basic hydrolysis of the other esters to the free acid, i.e. to compounds (1*) or (Ia*), in which R is in each case H, and subsequent esterification with an alcohol R⁴—OH.

Variants (c) and (c1):

The preparation of diastereomer mixtures or racemic diastereomers of the formula (I) according to variant (c) or optically active compounds (Ia) according to variant (c1) is therefore characterized in that a compound of the abovementioned formula (I*) or the formula (Ia*) in which the radicals R are each hydrogen (free carboxylic acids) is esterified with an alcohol of the formula R⁴—OH by customary methods, if appropriate combined with a previous preparation (c-1) or (c1-1) of the free acid from another ester of the formula (I*) or the formula (Ia*) in which the radicals R are each not hydrogen.

The esterification from the free acid of the formula (I*)/R═H or (Ia*)/R═H can be carried out, for example, analogously to customary methods, for example at temperatures of from 0° C. to 120° C., preferably from 20° C. to 50° C., optionally in the presence of a catalyst, in a substantially anhydrous medium or under conditions where the water including the water formed during the esterification is bound or otherwise removed. Suitable catalysts are anhydrous acids and bases, preferably organic acids or bases; see handbooks for chemical processes for esterifying carboxylic acids; see also, for example, J. Am. Chem. Soc. 2007, 129 (43), 13321; J. Org. Chem. 1984, 49 (22), 4287.

Suitable solvents for the esterification are the aprotic organic solvents mentioned above for process variants (b) and (b1), including the alcohol R⁴—OH which is at the same time used as a reaction partner for the esterification, optionally in combination with one of the aprotic organic solvents mentioned.

Suitable catalysts for the esterification are the bases or acidic or basic catalysts mentioned for mentioned process variant (a) (Michael addition), in anhydrous form or with a water content which is as low as possible. Preferred catalysts are the bases lithium hydroxide, potassium carbonate or organic amines such as pyridines, substituted pyridines and DBU.

Any hydrolysis carried out before the esterification [process variants (c-1) and (c1-1)] of other esters of the formula (I*) or the formula (Ia*), where R is in each case not H, can be carried out analogously to customary methods, for example at temperatures of from 0° C. to 120° C., preferably from 20° C. to 50° C., if appropriate in the presence of a catalyst, in a water-containing medium/solvent; see handbooks on chemical processes for hydrolysing carboxylic esters; see also, for example, J. Am. Chem. Soc. 2007, 129 (43), 13321; J. Org. Chem. 1984, 49 (22), 4287.

A suitable solvent for the hydrolysis [process variants (c-1) and (c1-1)] is water or a water-containing organic solvent, for example the organic solvent mentioned based on process variant (a) mentioned (Michael addition), preferably water or polar organic solvents containing water, such as THF.

Suitable catalysts for the hydrolysis are the acids, bases or acidic or basic catalysts mentioned for process variant (a) (Michael addition), in each case containing water. Preferred catalysts are aqueous acids and bases, in particular bases such as lithium hydroxide, sodium hydroxide, potassium carbonate, pyridines, substituted pyridines and DBU in the presence of organic solvents.

The catalysts for the esterification or the hydrolysis can generally be employed in catalytic amounts. In general, it is also possible to use relatively large amounts including equimolar amounts or in molar excess. Frequently, a use as solvent is also possible.

The reaction mixtures are worked up in a customary manner, for example by mixing with water, separating the phases and, if appropriate, chromatographic purification of the crude products. Some of the intermediates and end products are obtained in the form of colourless or slightly brownish viscous oils which are purified or freed from volatile components under reduced pressure and at moderately elevated temperature.

If the intermediates and end products are obtained as solids, the purification can also be carried out by recrystallization or digestion. If individual compounds (I) or (Ia) cannot be obtained by the routes described above, they can be prepared by derivatization of other compounds (I) or (Ia).

To prepare the erythro compounds, threo compounds or optically active erythro or threo compounds according to the invention, preferably the threo compounds (Ia), from the diastereomer mixtures of the compounds (I), it is necessary to enrich the respective diastereomer, for example the threo isomer or the stereoisomer (enantiomer) erythro-1, erythro-2, threo-1 or threo-2, preferably threo-2, from the mixture of the stereoisomers in an appropriate manner. Accordingly, an expedient process comprises the initial isolation of the erythro-1 and erythro-2 or threo isomers threo-1 and threo-2 from the diastereomer mixture of the compounds of the formula (I) which still comprises the other isomers, and optionally the subsequent optical resolution with isolation or enrichment of the enantiomer from the mixture with the other enantiomers.

The isolation of the diastereomers as a racemic mixture can be carried out analogously to the customary separation and purification processes mentioned above (diastereomer separation).

Suitable for the subsequent preparation of compounds of the optically active compounds (I), preferably for the formula (Ia), are methods for optical resolution generally known to the person skilled in the art from analogous cases (cf. handbooks of stereochemistry), for example following processes for separating mixtures into diastereomers, for example by physical processes, such as crystallization, chromatographic processes, in particular column chromatography and high-pressure liquid chromatography, distillation, if appropriate under reduced pressure, extraction and other processes, it is possible to separate remaining mixtures of enantiomers, generally by chromatographic separation on chiral solid phases. Suitable for preparative amounts or on an industrial scale are processes such as the crystallization of diastereomeric salts which can be obtained from the diastereomer mixtures using optically active acids and, if appropriate, provided that acidic groups are present, using optically active bases.

Optically active acids which are suitable for optical resolution by crystallization of diastereomeric salts are, for example, camphorsulphonic acid, camphoric acid, bromocamphorsulphonic acid, quinic acid, tartaric acid, dibenzoyltartaric acid and other analogous acids; suitable optically active bases are, for example, quinine, cinchonine, quinidine, brucine, 1-(S)- or 1-(R)-phenylethylamine and other analogous bases.

The crystallizations are then in most cases carried out in aqueous, alcoholic or aqueous-organic solvents, where the diastereomer which is less soluble precipitates first, if appropriate after seeding. One enantiomer of the compound of the formula (I) is then liberated from the precipitated salt, or the other is liberated from the crystals, by acidification or using a base.

Accordingly, the invention also provides the process for preparing the optically active compounds (I) [variant (d)], preferably (Ia), characterized in that

(d) an optical resolution is carried out with compounds (I), preferably the erythro compounds or in particular the threo compounds of the formula (I), and the desired enantiomer, preferably the compound (Ia), is isolated in a stereochemical purity of from 60 to 100%, preferably from 70 to 100%, more preferably from 80 to 100%, in particular from 90 to 100%, based on the mixture of the erythro and threo enantiomers present.

As an alternative to the optical resolution methods mentioned, enantioselective processes starting with stereochemically pure starting materials are in principle also suitable for preparing the optically active enantiomers, preferably the threo-2 enantiomers (Ia).

The following acids are generally suitable for preparing the acid addition salts of the compounds of the formula (I): hydrohalic acids, such as hydrochloric acid or hydrobromic acid, furthermore phosphoric acid, nitric acid, sulphuric acid, mono- or bifunctional carboxylic acids and hydroxycarboxylic acids, such as acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid, or lactic acid, and also sulphonic acids, such as p-toluenesulphonic acid and 1,5-naphthalenedisulphonic acid. The acid addition compounds of the formula (I) can be obtained in a simple manner by the customary methods for forming salts, for example by dissolving a compound of the formula (I) in a suitable organic solvent, such as, for example, methanol, acetone, methylene chloride or benzene, and adding the acid at temperatures of from 0 to 100° C., and they can be isolated in a known manner, for example by filtration, and, if appropriate, purified by washing with an inert organic solvent.

The base addition salts of the compounds of the formula (I) are preferably prepared in inert polar solvents, such as, for example, water, methanol or acetone, at temperatures of from 0 to 100° C. Examples of bases which are suitable for the preparation of the salts according to the invention are alkali metal carbonates, such as potassium carbonate, alkali metal hydroxides and alkaline earth metal hydroxides, for example NaOH or KOH, alkali metal hydrides and alkaline earth metal hydrides, for example NaH, alkali metal alkoxides and alkaline earth metal alkoxides, for example sodium methoxide or potassium tert-butoxide, or ammonia, ethanolamine or quaternary ammonium hydroxide of the formula [NRR′R″R′″]⁺OH⁻.

Collections of compounds of the formula (I) which can be synthesized by the aforementioned process can also be prepared in a parallel manner, it being possible for this to take place in a manual, partly automated or completely automated manner. In this connection, it is possible to automate the reaction procedure, the work-up or the purification of the products and/or intermediates. Overall, this is understood as meaning a procedure as described, for example, by S. H. DeWitt in “Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated Synthesis”, Volume 1, Verlag Escom, 1997, pages 69 to 77.

For the parallelized reaction procedure and workup it is possible to use a range of commercially available instruments, of the kind offered by, for example, the companies Stem Corporation, Woodrolfe Road, Tollesbury, Essex, CM9 8SE, England, or H+P Labortechnik GmbH, Bruckmannring 28, 85764 Oberschleiβheim, Germany. For the parallel purification of compounds (I) or of intermediates produced during the preparation, there are available, inter alia, chromatography apparatuses, for example from ISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA. The apparatuses listed allow a modular procedure in which the individual process steps are automated, but between the process steps manual operations have to be carried out. This can be circumvented by using partly or completely integrated automation systems in which the respective automation modules are operated, for example, by robots. Automation systems of this type can be acquired, for example, from Zymark Corporation, Zymark Center, Hopkinton, Mass. 01748, USA.

Besides the methods described here, the preparation of compounds of the formula (I) can take place completely or partially by solid-phase supported methods. For this purpose, individual intermediates or all intermediates in the synthesis or a synthesis adapted for the corresponding procedure are bound to a synthesis resin. Solid-phase-supported synthesis methods are described extensively in the specialist literature, for example Barry A. Bunin in “The Combinatorial Index”, Academic Press, 1998.

The use of solid-phase-supported synthesis methods permits a number of protocols, which are known from the literature and which for their part may be performed manually or in an automated manner, to be carried out. For example, the “teabag method” (Houghten, U.S. Pat. No. 4,631,211; Houghten et al., Proc. Natl. Acad. Sci, 1985, 82, 5131-5135) in which products from IRORI, 11149 North Torrey Pines Road, La Jolla, Calif. 92037, USA, are employed, may be semiautomated. The automation of solid-phase-supported parallel syntheses is performed successfully, for example, by apparatuses from Argonaut Technologies, Inc., 887 Industrial Road, San Carlos, Calif. 94070, USA or MultiSynTech GmbH, Wullener Feld 4, 58454 Witten, Germany.

The preparation according to the processes described herein produces compounds of the formula (I) in the form of substance collections or libraries. Accordingly, the present invention also provides libraries of compounds of the formula (I) which comprise at least two compounds of the formula (I), and precursors thereof.

The compounds of the formula (I) according to the invention (and/or their salts), above and hereinbelow also referred to together as “compounds according to the invention”, “compounds (I) according to the invention” or in short as “compounds (I)”, have excellent herbicidal efficacy against a broad spectrum of economically important monocotyledonous and dicotyledonous annual harmful plants. The active compounds also have good control over perennial harmful plants which are difficult to control and produce shoots from rhizomes, root stocks or other perennial organs.

The present invention therefore also relates to a method for controlling unwanted plants or for regulating the growth of plants, preferably in crops of plants, where one or more compound(s) according to the invention is/are applied to the plants (for example harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants), to the seed (for example grains, seeds or vegetative propagules such as tubers or shoot parts with buds), to the soil in or on which the plants grow (for example the soil of cropland or non-cropland) or to the area on which the plants grow (for example the area under cultivation). In this context, the compounds according to the invention can be applied for example in pre-sowing (if appropriate also by incorporation into the soil), pre-emergence or post-emergence. Specific examples may be mentioned of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention, without the enumeration being restricted to certain species.

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

When the compounds according to the invention are applied to the soil surface before germination, either the weed seedlings are prevented completely from emerging or the weeds grow until they have reached the cotyledon stage, but then stop growing and eventually, after three to four weeks have elapsed, die completely.

If the active ingredients are applied post-emergence to the green parts of the plants, growth stops after the treatment, and the harmful plants remain at the growth stage of the time of application, or die completely after a certain time, such that competition by the weeds, which is harmful to the crop plants, is thus eliminated very early and in a lasting manner.

Although the compounds according to the invention display an outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, in particular Zea and Triticum, are damaged only to an insignificant extent, or not at all, depending on the structure of the respective compound according to the invention and its application rate. For these reasons, the present compounds are very suitable for selective control of unwanted plant growth in plant crops such as agriculturally useful plants or ornamentals.

In addition, the compounds according to the invention (depending on their particular structure and the application rate deployed) have outstanding growth-regulating properties in crop plants. They intervene to regulate the plant's metabolism and can thus be used for controlled influence on plant constituents and to facilitate harvesting, for example by triggering desiccation and stunted growth. In addition, they are also suitable for general control and inhibition of unwanted vegetative growth without killing the plants. Inhibiting the vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops since for example lodging can be reduced, or prevented completely, hereby.

By virtue of their herbicidal and plant growth-regulating properties, the active compounds can also be used for control of harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. In general, the transgenic plants are distinguished by especially advantageous properties, for example by resistances to certain pesticides, mainly certain herbicides, resistances to plant diseases or causative organisms of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. Thus, transgenic plants are known whose starch content is increased, or whose starch quality is altered, or those where the harvested material has a different fatty acid composition.

It is preferred with a view to trangenic crops to use the compounds according to the invention and/or their salts in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, millet, rice and corn or else crops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas and other vegetables.

It is preferred to employ the compounds according to the invention as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

By virtue of their herbicidal and plant-growth-regulatory properties, the active compounds can also be employed for controlling harmful plants in crops of known genetically modified plants or genetically modified plants still to be developed. In general, the transgenic plants are distinguished by especially advantageous properties, for example by resistances to certain pesticides, mainly certain herbicides, resistances to plant diseases or causative organisms of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. Thus, transgenic plants are known whose starch content is increased, or whose starch quality is altered, or those where the harvested material has a different fatty acid composition. Other particular properties may be tolerance or resistance to abiotic stressors, for example heat, low temperatures, drought, salinity and ultraviolet radication.

It is preferred to use the compounds of the formula (I) according to the invention or salts thereof in economically important transgenic crops of useful plants and ornamental plants, for example of cereals such as wheat, barley, rye, oats, millet, rice, cassaya and corn or else crops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas and other vegetables.

It is preferred to employ the compounds of the formula (I) according to the invention as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

Conventional ways of producing novel plants which have modified properties in comparison to plants which have occurred to date consist, for example, in traditional breeding methods and the generation of mutants. Alternatively, novel plants with altered properties can be generated with the aid of recombinant methods (see, for example, EP-A-0221044, EP-A-0131624). For example, the following have been described in several cases:

-   -   recombinant modifications of crop plants for the purpose of         modifying the starch synthesized in the plants (for example WO         92/11376, WO 92/14827, WO 91/19806).     -   transgenic crop plants which are resistant to particular         herbicides of the glufosinate type (cf., for example,         EP-A-0242236, EP-A-242246) or glyphosate type (WO 92/00377) or         the sulphonylureas (EP-A-0257993, U.S. Pat. No. 5,013,659),     -   transgenic crop plants, for example cotton, which is capable of         producing Bacillus thuringiensis toxins (Bt toxins), which make         the plants resistant to certain pests (EP-A-0142924,         EP-A-0193259),     -   transgenic crop plants with a modified fatty acid composition         (WO 91/13972),     -   genetically modified crop plants with novel constituents or         secondary metabolites, for example novel phytoalexins, which         bring about an increased disease resistance (EPA 309862,         EPA0464461),     -   genetically modified plants with reduced photorespiration which         feature higher yields and higher stress tolerance (EPA 0305398),     -   transgenic crop plants which produce pharmaceutically or         diagnostically important proteins (“molecular pharming”),     -   transgenic crop plants which are distinguished by higher yields         or better quality,     -   transgenic crop plants which are distinguished by a combination,         for example of the abovementioned novel properties (“gene         stacking”).

A large number of molecular-biological techniques by means of which novel transgenic plants with modified properties can be generated are known in principle; see, for example, I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg. or Christou, “Trends in Plant Science” 1 (1996) 423-431.

For such recombinant manipulations, nucleic acid molecules which allow mutagenesis or a sequence change by recombination of DNA sequences can be introduced into plasmids. For example, base substitutions can be carried out, part-sequences can be removed, or natural or synthetic sequences may be added with the aid of standard methods. For the joining of the DNA fragments to one another, adaptors or linkers can be attached to the fragments; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Gene and Klone” [Genes and Clones], VCH Weinheim 2nd edition 1996.

For example, the generation of plant cells with a reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect or by expressing at least one suitably constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product. For this purpose, it is firstly possible to use DNA molecules which comprise the entire coding sequence of a gene product including any flanking sequences present, or else DNA molecules which comprise only parts of the coding sequence, in which case these parts must be long enough to bring about an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.

When expressing nucleic acid molecules in plants, the protein synthesized may be localized in any desired compartment of the plant cell. However, to achieve localization in a particular compartment, it is possible, for example, to link the coding region with DNA sequences which ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). The nucleic acid molecules can also be expressed in the organelles of the plant cells.

The transgenic plant cells can be regenerated by known techniques to give rise to entire plants. In principle, the transgenic plants may be plants of any desired plant species, i.e. both monocotyledonous and dicotyledonous plants.

Thus, it is possible to obtain transgenic plants whose properties are altered by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences, or expression of heterologous (=foreign) genes or gene sequences.

It is preferred to employ the compounds (I) according to the invention in transgenic crops which are resistant to growth regulators such as, for example, dicamba, or against herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or against herbicides from the group consisting of the sulphonylureas, glyphosate, glufosinate or benzoylisoxazoles and analogous active compounds.

On employment of the inventive active ingredients in transgenic crops, not only do the effects toward harmful plants observed in other crops occur, but often also effects which are specific to application in the particular transgenic crop, for example an altered or specifically widened spectrum of weeds which can be controlled, altered application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing of growth and yield of the transgenic crop plants.

The invention therefore also relates to the use of the compounds of the formula (I) according to the invention and/or their salts as herbicides for controlling harmful plants in crops of useful plants or ornamentals, optionally in transgenic crop plants. Preference is given to the use by the pre- or post-emergence method in cereals such as wheat, barley, rye, oats, millet and rice, in particular in wheat by the post-emergence method.

Preference is also given to the use by the pre- or post-emergence method in corn, in particular by the pre-emergence method in corn.

Preference is also given to the use by the pre- or post-emergence method in soybeans, in particular by the post-emergence method in soybeans.

The use according to the invention for the control of harmful plants or for growth regulation of plants also includes the case in which the active compound of the formula (I) or its salt is not formed from a precursor substance (“prodrug”) until after application on the plant, in the plant or in the soil.

The invention also provides the method (application method) for controlling harmful plants or for regulating the growth of plants which comprises applying an effective amount of one or more compounds of the formula (I) or salts thereof onto the plants (harmful plants, if appropriate together with the useful plants), plant seeds, the soil in which or on which the plants grow or the area under cultivation.

The compounds (I) according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in the customary formulations. The invention therefore also provides herbicidal and plant growth-regulating compositions which comprise compounds of the formula (I) and/or salts thereof.

The compounds of the formula (I) and/or salts thereof can be formulated in various ways according to which biological and/or physicochemical parameters are required. Possible formulations include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), seed-dressing products, granules for broadcasting and soil application, granules (GR) in the form of microgranules, sprayable granules, coated granules and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

These individual formulation types are known in principle and are described, for example, in: Winnacker-Küchler, “Chemische Technologie” [Chemical technology], volume 7, C. Hanser Verlag Munich, 4th ed. 1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y., 1973; K. Martens, “Spray Drying” Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.

The necessary formulation aids, such as inert materials, surfactants, solvents and further additives are likewise known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J., H. v. Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's, “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler, “Chemische Technologie”, volume 7, C. Hanser Verlag Munich, 4th ed. 1986.

Wettable powders are preparations which can be dispersed uniformly in water and, as well as the active compound, apart from a diluent or inert substance, also comprise surfactants of the ionic and/or nonionic type (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulphates, alkanesulphonates, alkylbenzenesulphonates, sodium lignosulphonate, sodium 2,2′-dinaphthylmethane-6,6′-disulphonate, sodium dibutylnaphthalenesulphonate or else sodium oleoylmethyltaurinate. To prepare the wettable powders, the herbicidally active compounds are ground finely, for example in customary apparatus such as hammer mills, blower mills and air-jet mills, and simultaneously or subsequently mixed with the formulation assistants.

Emulsifiable concentrates are produced by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else relatively high-boiling aromatics or hydrocarbons or mixtures of the organic solvents, with addition of one or more surfactants of the ionic and/or nonionic type (emulsifiers). The emulsifiers used may, for example, be: alkylarylsulphonic calcium salts, such as calcium dodecylbenzenesulphonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, such as, for example, sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, such as, for example, polyoxyethylene sorbitan fatty acid esters.

Dusting products are obtained by grinding the active compound with finely distributed solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water- or oil-based. They can be produced, for example, by wet grinding by means of commercial bead mills with optional addition of surfactants as already listed above, for example, for the other formulation types.

Emulsions, e.g. oil-in-water emulsions (EW), can be prepared, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and if appropriate surfactants, as have for example already been listed above in connection with the other types of formulation.

Granules can be produced either by spraying the active compound onto adsorptive granulated inert material or by applying active compound concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils, to the surface of carrier substances, such as sand, kaolinites or of granulated inert material. Suitable active compounds can also be granulated in the manner customary for the production of fertilizer granules—if desired as a mixture with fertilizers.

Water-dispersible granules are produced generally by the customary processes such as spray-drying, fluidized bed granulation, pan granulation, mixing with high-speed mixers and extrusion without solid inert material.

For the production of pan granules, fluidized bed granules, extruder granules and spray granules, see, for example, processes in “Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; J. E. Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff.; “Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.

For further details regarding the formulation of crop protection agents, see, for example, G. C. Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

The agrochemical formulations comprise generally from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of active compound of the formula (I) and/or salts thereof.

In wettable powders, the active compound concentration is, for example, about 10 to 90% by weight; the remainder to 100% by weight consists of the customary formulation constituents. In emulsifiable concentrates, the active ingredient concentration may be about 1 to 90% and preferably 5 to 80% by weight. Dust-type formulations contain from 1 to 30% by weight of active compound, preferably usually from 5 to 20% by weight of active compound; sprayable solutions contain from about 0.05 to 80% by weight, preferably from 2 to 50% by weight of active compound. In the case of water-dispersible granules, the active compound content depends partly on whether the active compound is present in liquid or solid form and on which granulation assistants, fillers, etc., are used. In the water-dispersible granules, the content of active compound is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.

In addition, the active ingredient formulations mentioned optionally comprise the respective customary tackifiers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents which influence the pH and the viscosity. Examples of formulation auxiliaries are described, inter alia, in “Chemistry and Technology of Agrochemical Formulations”, ed. D. A. Knowles, Kluwer Academic Publishers (1998).

The compounds of the formula (I) or salts thereof can be employed as such or in the form of their preparations (formulations) combined with other pesticidally active compounds, such as, for example, insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and/or growth regulators, for example as finished formulation or as tank mixes. The combination formulations can be prepared on the basis of the abovementioned formulations, while taking account of the physical properties and stabilities of the active compounds to be combined.

Combination partners for the compounds according to the invention in mixed formulations or in the tank mix are, for example, known active compounds which are based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoen desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as are described in, for example, Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 15th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006 and the literature cited therein. Known herbicides or plant growth regulators which can be combined with the compounds according to the invention are, for example, the following active compounds (the compounds are either designated by the common name according to the International Organization for Standardization (ISO) or by the chemical name, or by the code number) and always comprise all use forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers. In this case, one or else, in some cases, more than one use form is mentioned by way of example: acetochlor, acibenzolar, acibenzolar-5-methyl, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryne, amicarbazone, amidochlor, amidosulphuron, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammonium sulphamate, ancymidol, anilofos, asulam, atrazine, azafenidin, azimsulphuron, aziprotryne, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulide, bensulphuron, bensulphuron-methyl, bentazone, benzfendizone, benzobicyclon, benzofenap, benzofluor, benzoylprop, bicyclopyrone, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromuron, buminafos, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorazifop, chlorazifop-butyl, chlorbromuron, chlorbufam, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlormequat-chloride, chlornitrofen, chlorophthalim, chlorthal-dimethyl, chlortoluron, chlorsulphuron, cinidon, cinidon-ethyl, cinmethylin, cinosulphuron, clethodim, clodinafop, clodinafop-propargyl, clofencet, clofencet-potassium, clomazone, clomeprop, cloprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cyclanilide, cycloate, cyclosulphamuron, cycloxydim, cycluron, cyhalofop, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, 2,4-D, 2,4-DB, daimuron/dymron, dalapon, daminozide, dazomet, n-decanol, desmedipham, desmetryn, detosyl-pyrazolate (DTP), diallate, dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, diethatyl, diethatyl-ethyl, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dikegulac-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimetrasulphuron, dinitramine, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, diquat-dibromide, dithiopyr, diuron, DNOC, eglinazine-ethyl, endothal, EPTC, esprocarb, ethalfluralin, ethametsulphuron, ethametsulphuron-methyl, ethephon, ethidimuron, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulphuron, etobenzanid, F-5331, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulphonamide, F-7967, i.e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulphone, fentrazamide, fenuron, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulphuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucarbazone-sodium, flucetosulphuron, fluchloralin, flufenacet (thiafluamide), flufenpyr, flufenpyr-ethyl, flumetralin, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl, flupoxam, flupropacil, flupropanate, flupyrsulphuron, flupyrsulphuron-methyl-sodium, flurenol, flurenol-butyl, fluridone, fluorochloridone, fluoroxypyr, fluoroxypyr-meptyl, flurprimidol, flurtamone, fluthiacet, fluthiacet-methyl, fluthiamide, fomesafen, foramsulphuron, forchlorfenuron, fosamine, furyloxyfen, gibberellic acid, glufosinate, glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-isopropylammonium, H-9201, i.e. O-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropylphosphoramidothioate, halosafen, halosulphuron, halosulphuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. 1-(dimethoxyphosphoryl)ethyl (2,4-dichlorophenoxy)acetate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulphuron, inabenfide, indanofan, indaziflam, indoleacetic acid (IAA), 4-indol-3-ylbutyric acid (IBA), iodosulphuron, iodosulphuron-methyl-sodium, iofensulphuron, iofensulphuron-sodium, ioxynil, ipfencarbazone, isocarbamid, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, KUH-043, i.e. 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulphonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, karbutilate, ketospiradox, lactofen, lenacil, linuron, maleic hydrazide, MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, mecoprop-butotyl, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide, mepiquat-chloride, mesosulphuron, mesosulphuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazasulphuron, methazole, methiopyrsulphuron, methiozolin, methoxyphenone, methyldymron, 1-methylcyclopropene, methyl isothiocyanate, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulphuron, metsulphuron-methyl, molinate, monalide, monocarbamide, monocarbamide dihydrogensulphate, monolinuron, monosulphuron, monosulphuron ester, monuron, MT-128, i.e. 6-chloro-N-[(2E)-3-chloroprop-2-en-1-yl]-5-methyl-N-phenylpyridazine-3-amine, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, naproanilide, napropamide, naptalam, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon, nicosulphuron, nipyraclofen, nitralin, nitrofen, nitrophenolate-sodium (isomer mixture), nitrofluorfen, nonanoic acid, norflurazon, orbencarb, orthosulphamuron, oryzalin, oxadiargyl, oxadiazon, oxasulphuron, oxaziclomefone, oxyfluorfen, paclobutrazole, paraquat, paraquat dichloride, pelargonic acid (nonanoic acid), pendimethalin, pendralin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, picloram, picolinafen, pinoxaden, piperophos, pirifenop, pirifenop-butyl, pretilachlor, primisulphuron, primisulphuron-methyl, probenazole, profluazole, procyazine, prodiamine, prifluraline, profoxydim, prohexadione, prohexadione-calcium, prohydrojasmone, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulphuron, propyzamide, prosulphalin, prosulphocarb, prosulphuron, prynachlor, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulphotole, pyrazolynate (pyrazolate), pyrazosulphuron, pyrazosulphuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulphan, pyrithiobac, pyrithiobac-sodium, pyroxasulphone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulphuron, saflufenacil, secbumeton, sethoxydim, siduron, simazine, simetryn, SN-106279, i.e. methyl (2R)-2-({7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthyl}oxy)propanoate, sulcotrione, sulphallate (CDEC), sulphentrazone, sulphometuron, sulphometuron-methyl, sulphosate (glyphosate-trimesium), sulphosulphuron, SW-065, SYN-523, SYP-249, i.e. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e. 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, tebutam, tebuthiuron, tecnazene, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryne, thenylchlor, thiafluamide, thiazafluoron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone, thiencarbazone-methyl, thifensulphuron, thifensulphuron-methyl, thiobencarb, tiocarbazil, topramezone, tralkoxydim, triafamone, triallate, triasulphuron, triaziflam, triazofenamide, tribenuron, tribenuron-methyl, trichloroacetic acid (TCA), triclopyr, tridiphane, trietazine, trifloxysulphuron, trifloxysulphuron-sodium, trifluralin, triflusulphuron, triflusulphuron-methyl, trimeturon, trinexapac, trinexapac-ethyl, tritosulphuron, tsitodef, uniconazole, uniconazole-P, vernolate, ZJ-0862, i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, and the following compounds:

Of particular interest is the selective control of harmful plants in crops of useful plants and ornamentals. Although the compounds (I) according to the invention have already demonstrated very good to adequate selectivity in a large number of crops, in principle, in some crops and in particular also in the case of mixtures with other, less selective herbicides, phytotoxicities on the crop plants may occur. In this connection, combinations of compounds (I) according to the invention are of particular interest which comprise the compounds (I) or their combinations with other herbicides or pesticides and safeners. The safeners, which are used in an antidotically effective amount, reduce the phytotoxic side effects of the herbicides/pesticides employed, for example in economically important crops, such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, oilseed rape, cotton and soybeans, preferably cereals. The following groups of compounds are suitable, for example, as safeners for the compounds (I) and their combinations with further pesticides:

A) compounds of the formula (S-I)

where the symbols and indices have the following meanings:

-   n_(A) is a natural number from 0 to 5, preferably from 0 to 3; -   R_(A) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, nitro or     (C₁-C₄)-haloalkyl; -   W_(A) is an unsubstituted or substituted divalent heterocyclic     radical from the group consisting of the partially unsaturated or     aromatic five-membered heterocycles having 1 to 3 ring heteroatoms     of the N or O type, where at least one nitrogen atom and at most one     oxygen atom is present in the ring, preferably a radical from the     group consisting of (W_(A) ¹) to (W_(A) ⁴),

-   m_(A) is 0 or 1; -   R_(A) ² is OR_(A) ³, SR_(A) ³ or NR_(A) ³R_(A) ⁴ or a saturated -    or unsaturated 3- to 7-membered heterocycle having at least one     nitrogen atom and up to 3 heteroatoms, preferably from the group     consisting of O and S, which is joined to the carbonyl group in     (S-1) via the nitrogen atom and is unsubstituted or substituted by     radicals from the group consisting of (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy     or optionally substituted phenyl, preferably a radical of the     formula OR_(A) ³, NH R_(A) ⁴ or N(CH₃)₂, especially of the formula     OR_(A) ³; -   R_(A) ³ is hydrogen or an unsubstituted or substituted aliphatic     hydrocarbyl radical preferably having a total of 1 to 18 carbon     atoms; -   R_(A) ⁴ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy or substituted or     unsubstituted phenyl; -   R_(A) ⁵ is H, (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl,     (C₁-C₄)-alkoxy(C₁-C₈)-alkyl, cyano or COOR_(A) ⁹ in which R_(A) ⁹ is     hydrogen, (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl,     (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-hydroxyalkyl,     (C₃-C₁₂)-cycloalkyl or tri-(C₁-C₄)-alkylsilyl; -   R_(A) ⁶, R_(A) ⁷, R_(A) ⁸ are identical or different and are     hydrogen, (C₁-C₈)-alkyl, -    (C₁-C₈)-haloalkyl, (C₃-C₁₂)-cycloalkyl or substituted or     unsubstituted phenyl;     preferably: -   a) compounds of the type of the     dichlorophenylpyrazoline-3-carboxylic acid, preferably compounds     such as ethyl     1-2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate     (S1-1) (“mefenpyr-diethyl”, see Pestic. Man.), and related compounds     as described in WO 91/07874; -   b) derivatives of dichlorophenylpyrazolecarboxylic acid, preferably     compounds such as ethyl     1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl     1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3),     ethyl     1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate     (S1-4), ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate     (S1-5) and related compounds as described in EP-A-333 131 and     EP-A-269 806; -   c) compounds of the triazolecarboxylic acid type, preferably     compounds such as fenchlorazole(-ethyl), i.e. ethyl     1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate     (S1-6), and related compounds as described in EP-A-174 562 and     EP-A-346 620; -   d) compounds of the type of the 5-benzyl- or     5-phenyl-2-isoxazoline-3-carboxylic acid or the     5,5-diphenyl-2-isoxazoline-3-carboxylic acid, preferably compounds     such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate     (S1-7) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-8) and     related compounds, as described in WO 91/08202, or ethyl     5,5-diphenyl-2-isoxazolinecarboxylate (S1-9) (“isoxadifen-ethyl”) or     n-propyl 5,5-diphenyl-2-isoxazolinecarboxylate (S1-10) or ethyl     5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-11), as     described in the patent application WO-A-95/07897.     B) Quinoline derivatives of the formula (S-II)

where the symbols and indices have the following meanings:

-   R_(B) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, nitro or     (C₁-C₄)-haloalkyl; -   n_(B) is a natural number from 0 to 5, preferably from 0 to 3; -   R_(B) ² is OR_(B) ^(S), SR_(B) ³ or NR_(B) ³R_(B) ⁴ or a saturated     or unsaturated 3- to 7-membered heterocycle having at least one     nitrogen atom and up to 3 heteroatoms, preferably from the group     consisting of O and S, which is joined to the carbonyl group in     (S-II) via the nitrogen atom and is unsubstituted or substituted by     radicals from the group consisting of (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy     or optionally substituted phenyl, preferably a radical of the     formula OR_(B) ³, NH R^(e) or N(CH₃)₂, especially of the formula     OR_(B) ³; -   R_(B) ³ is hydrogen or an unsubstituted or substituted aliphatic     hydrocarbyl radical preferably having a total of 1 to 18 carbon     atoms; -   R_(B) ⁴ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy or substituted or     unsubstituted phenyl; -   T_(B) is a (C₁ or C₂)-alkanediyl chain which is unsubstituted or     substituted by one or two (C₁-C₄)-alkyl radicals or by     [(C₁-C₃)-alkoxy]carbonyl;     preferably: -   a) compounds of the 8-quinolinoxyacetic acid type (S2), preferably -    1-methylhexyl 5-chloro-8-quinolinoxyacetate (common name     “cloquintocet-mexyl” (S2-1) (see Pestic. Man.), -    1,3-dimethylbut-1-yl 5-chloro-8-quinolinoxyacetate (S2-2), -    4-allyloxybutyl 5-chloro-8-quinolinoxyacetate (S2-3), -    1-allyloxyprop-2-yl 5-chloro-8-quinolinoxyacetate (S2-4), -    ethyl 5-chloro-8-quinolinoxyacetate (S2-5), -    methyl 5-chloro-8-quinolinoxyacetate (S2-6), -    allyl 5-chloro-8-quinolinoxyacetate (S2-7), -    2-(2-propylideneiminoxy)-1-ethyl 5-chloro-8-quinolinoxyacetate     (S2-8), 2-oxoprop-1-yl 5-chloro-8-quinolinoxyacetate (S2-9) and     related compounds as described in EP-A-86 750, EP-A-94 349 and     EP-A-191 736 or EP-A-0 492 366, and also their hydrates and salts as     described in WO-A-2002/034048. -   b) compounds of the (5-chloro-8-quinolinoxy)malonic acid type,     preferably compounds such as diethyl     (5-chloro-8-quinolinoxy)malonate, diallyl     (5-chloro-8-quinolinoxy)malonate, methyl ethyl     (5-chloro-8-quinolinoxy)malonate and related compounds, as described     in EP-A-0 582 198. -   C) Compounds of the formula (S-III)

where the symbols and indices have the following meanings:

-   R_(C) ¹ is (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,     (C₂-C₄)-haloalkenyl, (C₃-C₇)-cycloalkyl, preferably dichloromethyl; -   R_(C) ², R_(C) ³ are identical or different and are hydrogen,     (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, (C₁-C₄)-haloalkyl,     (C₂-C₄)-haloalkenyl, (C₁-C₄)-alkylcarbamoyl-(C₁-C₄)-alkyl,     (C₂-C₄)-alkenylcarbamoyl-(C₁-C₄)-alkyl,     (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, dioxolanyl-(C₁-C₄)-alkyl, thiazolyl,     furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted     phenyl, or R_(C) ² and R_(C) ³ together form a substituted or     unsubstituted heterocyclic ring, -    preferably an oxazolidine, thiazolidine, piperidine, morpholine, -    hexahydropyrimidine or benzoxazine ring;     preferably: -    active compounds of the dichloroacetamide type which are frequently     used as pre-emergence safeners (soil-active safeners), such as, for     example, “dichlormid” (see Pestic. Man.)     (=N,N-diallyl-2,2-dichloroacetamide), -    “R-29148” (=3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine from     Stauffer), -    “R-28725” (=3-dichloroacetyl-2,2,-dimethyl-1,3-oxazolidine from     Stauffer), “benoxacor” (see Pestic. Man.)     (=4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine), -    “PPG-1292” (=N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide     from PPG Industries), -    “DKA-24” (=N-allyl-N—[(allylaminocarbonyl)methyl]dichloroacetamide     from Sagro-Chem), -    “AD-67” or “MON 4660”     (=3-dichloroacetyl-1-oxa-3-azaspiro[4,5]decane from Nitrokemia or     Monsanto), -    “TI-35” (=1-dichloroacetylazepane from TRI-Chemical RT) -    “diclonon” (dicyclonon) or “BAS145138” or “LAB145138”     (=3-dichloroacetyl-2,5,5-trimethyl-1,3-diazabicyclo[4.3.0]nonane     from BASF) and -    “furilazole” or “MON 13900” (see Pestic. Man.)     (=(RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine)     D) N-Acylsulphonamides of the formula (S-IV) and their salts

in which

-   R_(D) ¹ is hydrogen, a hydrocarbon radical, a hydrocarbonoxy     radical, a hydrocarbonthio radical or a heterocyclyl radical which     is preferably attached via a carbon atom, where each of the 4     last-mentioned radicals is unsubstituted or substituted by one or     more identical or different radicals from the group consisting of     halogen, cyano, nitro, amino, hydroxy, carboxy, formyl, carboxamide,     sulphonamide and radicals of the formula —Z^(a)—R^(a), -    where each hydrocarbon moiety has preferaby 1 to 20 carbon atoms     and a carbon-containing radical R_(D) ¹ including substituents has     preferably 1 to 30 carbon atoms; -   R_(D) ² is hydrogen or (C₁-C₄)-alkyl, preferably hydrogen, or -   R_(D) ¹ and R_(D) ² together with the group of the formula —CO—N—     are the radical of a 3- to 8-membered saturated or unsaturated ring; -   R_(D) ³ are identical or different and are halogen, cyano, nitro,     amino, hydroxy, carboxy, formyl, CON H₂, SO₂NH₂ or a radical of the     formula —Z^(b)—R^(b); -   R_(D) ⁴ is hydrogen or (C₁-C₄)-alkyl, preferably H; -   R_(D) ⁵ are identical or different and are halogen, cyano, nitro,     amino, hydroxy, carboxy, CHO, CON H₂, SO₂NH₂ or a radical of the     formula —Z^(c)—R^(c); -   R^(a) is a hydrocarbon radical or a heterocyclyl radical, where each     of the two last-mentioned radicals is unsubstituted or substituted     by one or more identical or different radicals from the group     consisting of halogen, cyano, nitro, amino, hydroxyl, mono- and     di-[(C₁-C₄)-alkyl]amino, or an alkyl radical in which a plurality,     preferably 2 or 3, non-adjacent CH₂ groups are in each case replaced     by an oxygen atom; -   R^(b), R^(c) are identical or different and are a hydrocarbon     radical or a heterocyclyl radical, where each of the two     last-mentioned radicals is unsubstituted or substituted by one or     more identical or different radicals from the group consisting of     halogen, cyano, nitro, amino, hydroxy, phosphoryl,     halo-(C₁-C₄)-alkoxy, mono- and di-[(C₁-C₄)-alkyl]amino, or an alkyl     radical in which a plurality, preferably 2 or 3, non-adjacent CH₂     groups are in each case replaced by an oxygen atom; -   Z^(a) is a divalent group of the formula —O—, —S—, —CO—, —CS—,     —CO—O—, —CO—S—, —O—CO—, —S—CO—, —SO—, —SO₂—, —NR*—, —CO—NR*—,     —NR*—CO—, —SO₂—NR*— or —NR*—SO₂—, where the bond indicated on the     right-hand side of the divalent group in question is the bond to the     radical R^(a) and where the R* in the 5 last-mentioned radicals     independently of one another are each H, (C₁-C₄)-alkyl or     halo-(C₁-C₄)-alkyl; -   Z^(b), Z^(c) are independently of one another a direct bond or a     divalent group of the formula —O—, -5-, —CO—, —CS—, —CO—O—, —CO—S—,     —O—CO—, -    —S—CO—, —SO—, —SO₂—, —NR*—, —SO₂—NR*—, —NR*—SO₂—, —CO—NR*— -    or —NR*—CO—, where the bond indicated at the right-hand side of the     divalent group in question is the bond to the radical R^(b) or R^(c)     and where the R* in the 5 last-mentioned radicals independently of     one another are each H, (C₁-C₄)-alkyl or halo-(C₁-C₄)-alkyl; -   n_(D) is an integer from 0 to 4, preferably 0, 1 or 2, particularly     preferably 0 or 1, and -   m_(D) is an integer from 0 to 5, preferably 0, 1, 2 or 3, in     particular 0, 1 or 2;     E) acylsulphamoylbenzamides of the formula (S-V), if appropriate     also in salt form,

in which

-   X_(E) is CH or N, -   R_(E) ¹ is hydrogen, heterocyclyl or a hydrocarbon radical, where     the two last-mentioned radicals are optionally substituted by one or     more identical or different radicals from the group consisting of     halogen, cyano, nitro, amino, hydroxy, carboxy, CHO, CONH₂, SO₂NH₂     and Z^(a)—R^(a); -   R_(E) ² is hydrogen, hydroxy, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,     (C₂-C₆)-alkynyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, where the five     last-mentioned radicals are optionally substituted by one or more     identical or different radicals from the group consisting of     halogen, hydroxy, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and     (C₁-C₄)-alkylthio, or -   R_(E) ¹ and R_(E) ² together with the nitrogen atom that carries     them are a 3- to 8-membered saturated or unsaturated ring; -   R_(E) ³ is halogen, cyano, nitro, amino, hydroxy, carboxy, CHO,     CONH₂, SO₂NH₂ or Z^(b)—R¹³, -   R_(E) ⁴ is hydrogen, (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl or     (C₂-C₄)-alkynyl; -   R_(E) ⁵ is halogen, cyano, nitro, amino, hydroxy, carboxy,     phosphoryl, CHO, CONH₂, SO₂NH₂ or Z^(c)—R^(c); -   R^(a) is a (C₂-C₂₀)-alkyl radical whose carbon chain is interrupted     once or more than once by -    oxygen atoms, is heterocyclyl or a hydrocarbon radical, where the     two last-mentioned radicals are optionally substituted by one or     more identical or different radicals from the group consisting of     halogen, cyano, nitro, amino, hydroxyl, mono- and     di-[(C₁-C₄)-alkyl]-amino; -   R^(b), R^(c) are identical or different and are a (C₂-C₂₀)-alkyl     radical whose carbon chain is interrupted once or more than once by     oxygen atoms, are heterocyclyl or a hydrocarbon radical, where the     two last-mentioned radicals are optionally substituted by one or     more identical or different radicals from the group consisting of     halogen, cyano, nitro, amino, hydroxyl, phosphoryl,     (C₁-C₄)-haloalkoxy, mono- and di-[(C₁-C₄)-alkyl]amino; -   Z^(a) is a divalent unit from the group consisting of O, S, CO, CS,     C(O)O, C(O)S, SO, SO₂, NR^(d), C(O)NR^(d) and SO₂NR^(d); -   Z^(b), Z^(c) are identical or different and are a direct bond or     divalent unit from the group consisting of -    O, S, CO, CS, C(O)O, C(O)S, SO, SO₂, NR^(d), SO₂NR^(d) and     C(O)NR^(d); -   R^(d) is hydrogen, (C₁-C₄)-alkyl or (C₁-C₄)-haloalkyl; -   n_(E) is an integer from 0 to 4, and -   m_(E) if X is CH, is an integer from 0 to 5, and, if X is N, is an     integer from 0 to 4; -    from among these, preference is given to compounds (also in the     form of their salts) of the type of the acylsulphamoylbenzamides,     for example of the formula (S-VI) below, which are known, for     example, from WO 99/16744,

-    for example those in which -    R_(E) ¹=cyclopropyl and R_(E) ⁵=2-OMe (“cyprosulphamide”, S3-1), -    R_(E) ¹=cyclopropyl and R_(E) ⁵=5-Cl-2-OMe (S3-2), R_(E) ¹=ethyl     and R_(E) ⁵=2-OMe (S3-3), -    R_(E) ¹=isopropyl and R_(E) ⁵=5-Cl-2-OMe (S3-4) and -    R_(E) ¹=isopropyl and R_(E) ⁵=2-OMe (S3-5);     F) compounds of the type of the N-acylsulphamoylphenylureas of the     formula (S-VII), which are known, for example, from EP-A-365484

in which

-   A is a radical from the group consisting of

-   R_(F) ¹ and R_(F) ² independently of one another are hydrogen,     (C₁-C₈)-alkyl, (C₃-C₈)-cycloalkyl, (C₃-C₆)-alkenyl, (C₃-C₆)-alkynyl,

-    or (C₁-C₄)Alkoxy substituted by

-    or (C₁-C₄)Alkoxy, or -   R_(F) ¹ and R_(F) ² together are a (C₄-C₆)-alkylene bridge and a     (C₄-C₆)-alkylene bridge interrupted by oxygen, sulphur, SO, SO₂, NH     or —N(C₁-C₄-alkyl)-, -   R_(F) ³ is hydrogen or (C₁-C₄)-alkyl, -   R_(F) ⁴ and R_(F) ⁵ independently of one another are hydrogen,     halogen, cyano, nitro, trifluoromethyl, C₁-C₄-alkyl, C₁-C₄-alkoxy,     C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,     —COOR^(j), —CONR^(k)R^(m), —COR^(n), —SO₂NR^(k)R^(m) or     —OSO₂—C₁-C₄-alkyl, or R^(a) and R^(b) together are a     (C₃-C₄)-alkylene bridge which may be substituted by halogen or     C₁-C₄-alkyl, or a (C₃-C₄)-alkenylene bridge which may be substituted     by halogen or (C₁-C₄)-alkyl, or a C₄-alkadienylene bridge which may     be substituted by halogen or (C₁-C₄)-alkyl, and -   R^(g) and R^(h) independently of one another are hydrogen, halogen,     C₁-C₄-alkyl, trifluoromethyl, methoxy, methylthio or —COOR^(j),     where -   R^(c) is hydrogen, halogen, (C₁-C₄)-alkyl or methoxy, -   R^(d) is hydrogen, halogen, nitro, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy,     (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl, (C₁-C₄)-alkylsulphonyl,     —COOR^(j) or —CONR^(k)R^(m), -   R^(e) is hydrogen, halogen, C₁-C₄-alkyl, —COOR^(j), trifluoromethyl     or methoxy, or R^(d) and R^(e) together are a (C₃-C₄)-alkylene     bridge, -   R^(f) is hydrogen, halogen or (C₁-C₄)-alkyl, -   R^(X) and R^(Y) independently of one another are hydrogen, halogen,     (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, —COOR⁴,     trifluoromethyl, nitro or cyano, -   R^(j), R^(k) and R^(m) independently of one another are hydrogen or     (C₁-C₄)-alkyl, -   R^(k) and R^(m) together are a (C₄-C₆)-alkylene bridge and a     (C₄-C₆)-alkylene bridge interrupted by oxygen, NH or     —N(C₁-C₄-alkyl)-, and -   R^(n) is (C₁-C₄)-alkyl, phenyl or phenyl substituted by halogen,     (C₁-C₄)-alkyl, methoxy, nitro or trifluoromethyl, -   from among these, preference is given to: -    1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3-methylurea, -    1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3,3-dimethylurea, -    1-[4-(N-4,5-dimethylbenzoylsulphamoyl)phenyl]-3-methylurea, -    1-[4-(N-naphthoylsulphamoyl)phenyl]-3,3-dimethylurea, including the     stereoisomers and agriculturally customary salts, -   G) active compounds from the class of the hydroxyaromatics and the     aromatic-aliphatic carboxylic acid derivatives, for example -    ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic     acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid,     4-fluorosalicyclic acid,     1,2-dihydro-2-oxo-6-trifluoromethylpyridine-3-carboxamide,     2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in     WO 2004084631, WO 2005015994, WO 2006007981, WO 2005016001; -   H) active compounds from the class of the     1,2-dihydroquinoxalin-2-ones, for example -   1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one,     1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-thione,     1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one     hydrochloride,     1-(2-methylsulphonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one,     as described in WO 2005112630, -   I) active compounds which, in addition to herbicidal action against     harmful plants, also have safener action on crop plants such as     rice, for example “dimepiperate” or “MY-93” (see Pestic. Man.)     (=S-1-methyl-1-phenylethyl piperidine-1-thiocarboxylate), which is     known as safener for rice against damage caused by the herbicide     molinate, -    “daimuron” or “SK 23” (see Pestic. Man.)     (=1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as     safener for rice against imazosulfuron herbicide damage, -    “cumyluron”=“JC-940”     (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see     JP-A-60087254), which is known as a safener for rice against damage     by some herbicides, -    “methoxyphenone” or “NK 049”     (=3,3′-dimethyl-4-methoxybenzophenone), which is known as safener     for rice against damage by some herbicides, -    “CSB” (=1-bromo-4-(chloromethylsulphonyl)benzene) (CAS Reg. No.     54091-06-4 from Kumiai), which is known as safener for rice against     damage by some herbicides, -   K) compounds of the formula (S-IX), as described in WO-A-1998/38856,

-    where the symbols and indices have the following meanings:     -   R_(K) ¹, R_(K) ² independently of one another are halogen,         (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,         (C₁-C₄)-alkylamino, di(C₁-C₄)-alkylamino, nitro;     -   A_(K) is COOR_(K) ³ or COOR_(K) ⁴     -   R_(K) ³, R_(K) ⁴ independently of one another are hydrogen,         (C₁-C₄)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₄)-alkynyl, cyanoalkyl,         (C₁-C₄)-haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl,         pyridinylalkyl and alkylammonium,     -   n_(K) ¹ is 0 or 1 and     -   n_(K) ², n_(K) ³ independently of one another are 0, 1 or 2;         preferably:         methyl (diphenylmethoxy)acetate (CAS reg no: 41858-19-9), -   L) compounds of the formula (S-X) -    as described in WO A-98/27049

where the symbols and indices have the following meanings:

-   X_(L) is CH or N, -   n_(L) if X═N, is an integer from 0 to 4 and if X═CH, is an integer     from 0 to 5, -   R_(L) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,     (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, nitro, (C₁-C₄)-alkylthio,     (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-alkoxycarbonyl, optionally     substituted phenyl, optionally substituted phenoxy, -   R_(L) ² is hydrogen or (C₁-C₄)-alkyl -   R_(L) ³ is hydrogen, (C₁-C₈)-alkyl, (C₁-C₄)-alkenyl,     (C₁-C₄)-alkynyl, or aryl, where each of the aforementioned     carbon-containing radicals is unsubstituted or substituted by one or     more, preferably up to three identical or different radicals from     the group consisting of halogen and alkoxy; or salts thereof. -   M) Active compounds from the class of the     3-(5-tetrazolylcarbonyl)-2-quinolones, for example -    1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-qui nolone     (CAS Reg. No. 219479-18-2),     1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone     (CAS Reg. No.: 95855-00-8), as described in WO-A-1999000020, -   N) compounds of the formula (S-XI) or (S-XII) -    as described in WO-A-2007023719 and WO-A-2007023764

-    in which -   R_(N) ¹ is halogen, (C₁-C₄)-alkyl, methoxy, nitro, cyano, CF₃, OCF₃, -   Y, Z independently of one another are O or S, -   n_(N) is an integer from 0 to 4, -   R_(N) ² is (C₁-C₁₆)-alkyl, (C₂-C₆)-alkenyl, (C₃-C₆)-cycloalkyl,     aryl; benzyl, halobenzyl, -   R_(N) ³ is hydrogen, (C₁-C₆)-alkyl; -   O) one or more compounds from the group consisting of: -    1,8-naphthalic anhydride, -    O,O-diethyl S-2-ethylthioethyl phosphorodithioate (disulfoton), -    4-chlorophenyl methylcarbamate (mephenate), -    O,Odiethyl O-phenyl phosphorothioate (dietholate), -    4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid (CL-304415, CAS     Reg. No.: 31541-57-8), -    2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate (MG-838,     CAS Reg. No.: 133993-74-5), -    methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate     (from WOA98/13361; CAS Reg. No.: 205121-04-6), -    cyanomethoxyimino(phenyl)acetonitrile (cyometrinil) -    1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile (oxabetrinil), -    4′-chloro-2,2,2-trifluoroacetophenone     0-1,3-dioxolan-2-ylmethyloxime (fluxofenim), -    4,6-dichloro-2-phenylpyrimidine (fenclorim), -    benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate     (flurazole), -    2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), -    including the stereoisomers possible in each case, and the salts     customary in agriculture.

The weight ratios of herbicide (mixture) to safener depend generally on the herbicide application rate and the efficacy of the safener in question and may vary within wide limits, for example in the range from 200:1 to 1:200, preferably 100:1 to 1:100, in particular 20:1 to 1:20. Analogously to the compounds (I) or mixtures thereof, the safeners can be formulated with further herbicides/pesticides and be provided and employed as a finished formulation or tankmix with the herbicides.

For application, the herbicide or herbicide/safener formulations present in commercial form are, if appropriate, diluted in a customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules with water. Preparations in the form of dusts, granules for soil application or granules for broadcasting and sprayable solutions are usually not diluted further with other inert substances prior to application.

The required application rate of the compounds of the formula (I) and/or their salts varies according to the external conditions such as, inter alia, temperature, humidity and the type of herbicide used. It can vary within wide limits. For the application as herbicide for controlling harmful plants, it is, for example, in the range of from 0.001 to 10.0 kg/ha or more of active substance, preferably in the range of from 0.005 to 5 kg/ha, in particular in the range of from 0.01 to 1 kg/ha, of active substance. This applies both to the pre-emergence and the post-emergence application.

When used as plant growth regulator, for example as culm stabilizer for crop plants like those mentioned above, preferably cereal plants, such as wheat, barley, rye, triticale, millet, rice or corn, the application rate is, for example, in the range of from 0.001 to 2 kg/ha or more of active substance, preferably in the range of from 0.005 to 1 kg/ha, in particular in the range of from 10 to 500 g/ha of active substance, very particularly from 20 to 250 g/ha of active substance. This applies both to application by the pre-emergence method and the post-emergence method, the post-emergence treatment generally being preferred.

The application as culm stabilizer may take place at various stages of the growth of the plants. Preferred is, for example, the application after the tillering phase, at the beginning of the longitudinal growth.

As an alternative, application as plant growth regulator is also possible by treating the seed, which includes various techniques for dressing and coating seed. Here, the application rate depends on the particular techniques and can be determined in preliminary tests.

In an exemplary manner, some synthesis examples of compounds of the general formula (I) are described below. In the examples, the amounts (including percentages) refer to the weight, unless especially stated otherwise.

The symbols “>” and “<” mean “greater than” and “smaller than”, respectively. The symbol “≧” means “greater than or equal to”, the symbol “≦” means “smaller than or equal to”.

If, in the context of the description and the examples, the terms “R” and “S” are given for the absolute configuration on a center of chirality of the stereoisomers of the formula (I), this RS nomenclature follows, unless defined differently, the Cahn-Ingold-Prelog rule.

(A) SYNTHESIS EXAMPLES Example A1 erythro- and threo-Methyl 4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoate (Table 2, Examples erythro-Ibb1082 and threo-Ibb1082)

Under protective gas (Ar), 0.055 g (1.015 mmol) of potassium tert-butoxide was added to 1.048 g (5.329 mmol) of methyl 3-(4-chlorophenyl)acrylate and 1.000 g (5.075 mmol) of (5-bromopyridin-3-yl)acetonitrile in 8.0 ml of toluene. 3 ml of dimethylformamide were added, and the mixture was stirred at 80° C. for 8 h. The solvent was removed under reduced pressure and the residue was taken up in dichloromethane and washed twice with in each case 25 ml of water. The combined organic phases were washed successively with 1N aqueous hydrochloric acid and with saturated aqueous sodium chloride solution and dried over sodium sulphate. The solvent was removed under reduced pressure. Chromatography of the residue on silica gel (gradient: starting with ethyl acetate/heptane=5:95 over the course of 20 minutes increased to ethyl acetate/heptane=30:70) gave, successively, 0.578 g (29% of theory) of threo-methyl 4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoate and 0.800 g (40% of theory) of erythro-methyl 4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoate. The configuration was assigned by comparison of the chemical shifts of the respective CHCN doublets at 4.12 ppm and 4.49 ppm, respectively, in the ¹H-NMR (CDCl₃). The lower-field signal was assigned to the erythro-diastereomer, analogously to the literature. ¹H-NMR in CDCl₃ see Table 2.

Example A2 Methyl (3S,4S)-4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoate (Table 2, Example threo-1-Ibb1082)

Preparative chromatography [(80 ml/min of n-heptane/2-propanol (70:30)] of the mixture, obtained in Example A1, of the racemic threo-methyl 4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoate on a chiral solid phase [Chiralpak IC, 20 μm, (250×50)-mm column] gave 232.0 mg of methyl (3S,4S)-4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoate [chemical purity >95% (NMR), isomeric purity >99% (chiral HPLC)], which was the first of the two stereoisomers to elute (retention time=12.17 min). Specific rotation [α]: +61°. For ¹H-NMR in CDCl₃ and retention time in analytical HPLC: see Table 2.

Example A3 Methyl (3R,4R)-4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoate (Table 2, Example threo-2-Ibb1082)

Preparative chromatography [(80 ml/min of n-heptane/2-propanol (70:30)] of the mixture, obtained in Example A1, of the racemic threo-methyl 4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoate on a chiral solid phase [Chiralpak IC, 20 μm, (250×50)-mm column] gave 73.0 mg of methyl (3R,4R)-4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoate [chemical purity >95% (NMR), isomeric purity >99% (chiral HPLC)], which was the last of the two stereoisomers to elute (retention time=20.01 min). Specific rotation [α]: −61°. For ¹H-NMR in CDCl₃ and retention time in analytical HPLC: see Table 2.

The compounds, described in tables below, of the absolute configuration (3R,4R) are obtained according to or analogously to the examples described above.

Example A4 4-Cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoic acid (Table 2, Examples Iba1082)

Under protective gas (Ar), 3.0 ml of 2 molar aqueous sodium hydroxide solution were added to 0.630 g (1.600 mmol) of methyl 4-cyano-3-(2,6-difluorophenyl)-4-(3,4-difluorophenyl)butanoate (Example A1) in 160 ml of methanol, and the mixture was stirred at 25° C. for 2 h. The methanol was removed under reduced pressure. The residue was acidified with 2N aqueous hydrochloric acid (pH=3). Filtration and drying of the residue under high vacuum at 40° C. gave 0.593 g (99.8% of theory) of the title compound as a colourless solid [(erythro:threo=35:65, comparison of the doublets in the ¹H-NMR in CDCl₃ at 4.14 (threo) and 4.50 ppm (erythro)]. ¹H-NMR in CDCl₃ see Table 2.

Example A5 Ethyl 4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoate (Table 2, Examples Ibc1082)

Under protective gas (Ar), 0.121 g (0.632 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide (EDC), a spatula tip of 4-dimethylaminopyridine (DMAP) and 0.061 g (1.317 mmol) of ethanol were added to 0.200 g (0.527 mmol) of 4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoic acid (Example A4) in 4 ml of dichloromethane, and the mixture was stirred at 25° C. for 8 h. The solvent was removed under reduced pressure and the residue was taken up in dichloromethane and washed twice with in each case 15 ml of water. The combined organic phases were dried over sodium sulphate and the solvent was removed under reduced pressure. Chromatography of the residue on silica gel (gradient: starting with ethyl acetate/heptane=5:95 over the course of 20 minutes increased to ethyl acetate/heptane=20:80) gave 0.143 g (67% of theory) of the title compound (erythro:threo=58:42). ¹H-NMR in CDCl₃ see Table 2.

The compounds described in the tables below are obtained according to or analogously to the examples described above.

In the tables:

-   Ex.=Example number -   H=hydrogen (atom) -   Me=methyl -   Et=ethyl -   n-Pr=n-propyl -   i-Pr=isopropyl -   rt=retention time -   F, Cl, Br, I=fluorine, chlorine, bromine and iodine, respectively,     in accordance with the conventional chemical atom symbol -   CN=cyano -   NO₂=nitro -   MeO or OMe=methoxy -   CF₃=trifluoromethyl -   OCF₃=trifluoromethoxy -   OCF₂H=diflluoromethoxy -   CO₂Me=methoxycarbonyl (“methylester group”)

The position of a substituent at the phenyl ring, for example in position 2, is stated as a prefix to the symbol or the abbreviation of the radical, for example

-   2-Cl=2-chloro -   2-F=2-fluoro

Numerations of the substituent positions for di- or trisubstituted substitution patterns are analogously stated as a prefix, for example

-   3,4-Me₂=3,4-dimethyl (e.g. as substitution at the phenyl ring) -   3,5-F₂=3,5-difluoro (e.g. as substitution at the phenyl ring) -   3,4-F₂=3,4-difluoro (e.g. as substitution at the phenyl ring)

Other abbreviations are to be understood analogously to the examples stated above.

-   “(R¹)_(m)=“H”=no substituent other than R³ present (m=0) -   “(R²)_(n)=“H”=unsubstituted cycle (n=0)

In addition, the customary chemical symbols and formulae apply, such as, for example, CH₂ for methylene or CF₃ for trifluoromethyl or OH for hydroxyl. Correspondingly, composite meanings are defined as composed of the abbreviations mentioned.

The retention times (“rt”) given for the compounds of Tables 2a-2f were obtained by analytical HPLC of the compounds (I) on a chiral solid phase. At a concentration of 1 mg/ml, the compounds of the formula (I) were dissolved in dichloromethane p.a. and directly subjected to HPLC. The chromatographically purified compounds (I) have a stereochemical purity of ≧90%.

TABLE 1 Definitions of structural combinations of groups (R¹)_(m), (R²)_(n) and R³ for the tables of compounds of the general formula (I) according to the invention below No. (R¹)_(m) (R²)_(n) R³ 1 H 4-F F 2 H 4-Cl F 3 H 4-Br F 4 H H F 5 H 4-Me F 6 H 4-CN F 7 H 4-NO₂ F 8 H 4-OMe F 9 H 3-F F 10 H 3-Cl F 11 H 3-Br F 12 H 3-Me F 13 H 3-CN F 14 H 3-NO₂ F 15 H 3-OMe F 16 H 2-F F 17 H 2-Cl F 18 H 2-Br F 19 H 2-Me F 20 H 2-CN F 21 H 2-NO₂ F 22 H 2-OMe F 23 H 2,3-F₂ F 24 H 2,4-F₂ F 25 H 2,5-F₂ F 26 H 2,6-F₂ F 27 H 3,4-F₂ F 28 H 3,5-F₂ F 29 H 2,3-Cl₂ F 30 H 2,4-Cl₂ F 31 H 2,5-Cl₂ F 32 H 2,6-Cl₂ F 33 H 3,4-Cl₂ F 34 H 3,5-Cl₂ F 35 H 2-F, 3-Cl F 36 H 2-F, 4-Cl F 37 H 2-F, 5-Cl F 38 H 2-F, 6-Cl F 39 H 2,6-F₂, 4-Cl F 40 H 3-F, 4-Cl F 41 H 3-Cl, 5-F F 42 H 2-Cl, 5-F F 43 H 3-CN, 4-Cl F 44 H 3-NO₂, 4-Cl F 45 H 2-F, 4-Br F 46 6-F 4-F F 47 6-F 4-Cl F 48 6-F 4-Br F 49 6-F H F 50 6-F 4-Me F 51 6-F 4-CN F 52 6-F 4-NO₂ F 53 6-F 4-OMe F 54 6-F 3-F F 55 6-F 3-Cl F 56 6-F 3-Br F 57 6-F 3-Me F 58 6-F 3-CN F 59 6-F 3-NO₂ F 60 6-F 3-OMe F 61 6-F 2-F F 62 6-F 2-Cl F 63 6-F 2-Br F 64 6-F 2-Me F 65 6-F 2-CN F 66 6-F 2-NO₂ F 67 6-F 2-OMe F 68 6-F 2,3-F₂ F 69 6-F 2,4-F₂ F 70 6-F 2,5-F₂ F 71 6-F 2,6-F₂ F 72 6-F 3,4-F₂ F 73 6-F 3,5-F₂ F 74 6-F 2,3-Cl₂ F 75 6-F 2,4-Cl₂ F 76 6-F 2,5-Cl₂ F 77 6-F 2,6-Cl₂ F 78 6-F 3,4-Cl₂ F 79 6-F 3,5-Cl₂ F 80 6-F 2-F, 3-Cl F 81 6-F 2-F, 4-Cl F 82 6-F 2-F, 5-Cl F 83 6-F 2-F, 6-Cl F 84 6-F 2,6-F₂, 4-Cl F 85 6-F 3-F, 4-Cl F 86 6-F 3-Cl, 5-F F 87 6-F 2-Cl, 5-F F 88 6-F 3-CN, 4-Cl F 89 6-F 3-NO₂, 4-Cl F 90 6-F 2-F, 4-Br F 91 6-Cl 4-F F 92 6-Cl 4-Cl F 93 6-Cl 4-Br F 94 6-Cl H F 95 6-Cl 4-Me F 96 6-Cl 4-CN F 97 6-Cl 4-NO₂ F 98 6-Cl 4-OMe F 99 6-Cl 3-F F 100 6-Cl 3-Cl F 101 6-Cl 3-Br F 102 6-Cl 3-Me F 103 6-Cl 3-CN F 104 6-Cl 3-NO₂ F 105 6-Cl 3-OMe F 106 6-Cl 2-F F 107 6-Cl 2-Cl F 108 6-Cl 2-Br F 109 6-Cl 2-Me F 110 6-Cl 2-CN F 111 6-Cl 2-NO₂ F 112 6-Cl 2-OMe F 113 6-Cl 2,3-F₂ F 114 6-Cl 2,4-F₂ F 115 6-Cl 2,5-F₂ F 116 6-Cl 2,6-F₂ F 117 6-Cl 3,4-F₂ F 118 6-Cl 3,5-F₂ F 119 6-Cl 2,3-Cl₂ F 120 6-Cl 2,4-Cl₂ F 121 6-Cl 2,5-Cl₂ F 122 6-Cl 2,6-Cl₂ F 123 6-Cl 3,4-Cl₂ F 124 6-Cl 3,5-Cl₂ F 125 6-Cl 2-F, 3-Cl F 126 6-Cl 2-F, 4-Cl F 127 6-Cl 2-F, 5-Cl F 128 6-Cl 2-F, 6-Cl F 129 6-Cl 2,6-F₂, 4-Cl F 130 6-Cl 3-F, 4-Cl F 131 6-Cl 3-Cl, 5-F F 132 6-Cl 2-Cl, 5-F F 133 6-Cl 3-CN, 4-Cl F 134 6-Cl 3-NO₂, 4-Cl F 135 6-Cl 2-F, 4-Br F 136 6-Br 4-F F 137 6-Br 4-Cl F 138 6-Br 4-Br F 139 6-Br H F 140 6-Br 4-Me F 141 6-Br 4-CN F 142 6-Br 4-NO₂ F 143 6-Br 4-OMe F 144 6-Br 3-F F 145 6-Br 3-Cl F 146 6-Br 3-Br F 147 6-Br 3-Me F 148 6-Br 3-CN F 149 6-Br 3-NO₂ F 150 6-Br 3-OMe F 151 6-Br 2-F F 152 6-Br 2-Cl F 153 6-Br 2-Br F 154 6-Br 2-Me F 155 6-Br 2-CN F 156 6-Br 2-NO₂ F 157 6-Br 2-OMe F 158 6-Br 2,3-F₂ F 159 6-Br 2,4-F₂ F 160 6-Br 2,5-F₂ F 161 6-Br 2,6-F₂ F 162 6-Br 3,4-F₂ F 163 6-Br 3,5-F₂ F 164 6-Br 2,3-Cl₂ F 165 6-Br 2,4-Cl₂ F 166 6-Br 2,5-Cl₂ F 167 6-Br 2,6-Cl₂ F 168 6-Br 3,4-Cl₂ F 169 6-Br 3,5-Cl₂ F 170 6-Br 2-F, 3-Cl F 171 6-Br 2-F, 4-Cl F 172 6-Br 2-F, 5-Cl F 173 6-Br 2-F, 6-Cl F 174 6-Br 2,6-F₂, 4-Cl F 175 6-Br 3-F, 4-Cl F 176 6-Br 3-Cl, 5-F F 177 6-Br 2-Cl, 5-F F 178 6-Br 3-CN, 4-Cl F 179 6-Br 3-NO₂, 4-Cl F 180 6-Br 2-F, 4-Br F 181 6-CN 4-F F 182 6-CN 4-Cl F 183 6-CN 4-Br F 184 6-CN H F 185 6-CN 4-Me F 186 6-CN 4-CN F 187 6-CN 4-NO₂ F 188 6-CN 4-OMe F 189 6-CN 3-F F 190 6-CN 3-Cl F 191 6-CN 3-Br F 192 6-CN 3-Me F 193 6-CN 3-CN F 194 6-CN 3-NO₂ F 195 6-CN 3-OMe F 196 6-CN 2-F F 197 6-CN 2-Cl F 198 6-CN 2-Br F 199 6-CN 2-Me F 200 6-CN 2-CN F 201 6-CN 2-NO₂ F 202 6-CN 2-OMe F 203 6-CN 2,3-F₂ F 204 6-CN 2,4-F₂ F 205 6-CN 2,5-F₂ F 206 6-CN 2,6-F₂ F 207 6-CN 3,4-F₂ F 208 6-CN 3,5-F₂ F 209 6-CN 2,3-Cl₂ F 210 6-CN 2,4-Cl₂ F 211 6-CN 2,5-Cl₂ F 212 6-CN 2,6-Cl₂ F 213 6-CN 3,4-Cl₂ F 214 6-CN 3,5-Cl₂ F 215 6-CN 2-F, 3-Cl F 216 6-CN 2-F, 4-Cl F 217 6-CN 2-F, 5-Cl F 218 6-CN 2-F, 6-Cl F 219 6-CN 2,6-F₂, 4-Cl F 220 6-CN 3-F, 4-Cl F 221 6-CN 3-Cl, 5-F F 222 6-CN 2-Cl, 5-F F 223 6-CN 3-CN, 4-Cl F 224 6-CN 3-NO₂, 4-Cl F 225 6-CN 2-F, 4-Br F 226 6-Me 4-F F 227 6-Me 4-Cl F 228 6-Me 4-Br F 229 6-Me H F 230 6-Me 4-Me F 231 6-Me 4-CN F 232 6-Me 4-NO₂ F 233 6-Me 4-OMe F 234 6-Me 3-F F 235 6-Me 3-Cl F 236 6-Me 3-Br F 237 6-Me 3-Me F 238 6-Me 3-CN F 239 6-Me 3-NO₂ F 240 6-Me 3-OMe F 241 6-Me 2-F F 242 6-Me 2-Cl F 243 6-Me 2-Br F 244 6-Me 2-Me F 245 6-Me 2-CN F 246 6-Me 2-NO₂ F 247 6-Me 2-OMe F 248 6-Me 2,3-F₂ F 249 6-Me 2,4-F₂ F 250 6-Me 2,5-F₂ F 251 6-Me 2,6-F₂ F 252 6-Me 3,4-F₂ F 253 6-Me 3,5-F₂ F 254 6-Me 2,3-Cl₂ F 255 6-Me 2,4-Cl₂ F 256 6-Me 2,5-Cl₂ F 257 6-Me 2,6-Cl₂ F 258 6-Me 3,4-Cl₂ F 259 6-Me 3,5-Cl₂ F 260 6-Me 2-F, 3-Cl F 261 6-Me 2-F, 4-Cl F 262 6-Me 2-F, 5-Cl F 263 6-Me 2-F, 6-Cl F 264 6-Me 2,6-F₂, 4-Cl F 265 6-Me 3-F, 4-Cl F 266 6-Me 3-Cl, 5-F F 267 6-Me 2-Cl, 5-F F 268 6-Me 3-CN, 4-Cl F 269 6-Me 3-NO₂, 4-Cl F 270 6-Me 2-F, 4-Br F 271 6-OMe 4-F F 272 6-OMe 4-Cl F 273 6-OMe 4-Br F 274 6-OMe H F 275 6-OMe 4-Me F 276 6-OMe 4-CN F 277 6-OMe 4-NO₂ F 278 6-OMe 4-OMe F 279 6-OMe 3-F F 280 6-OMe 3-Cl F 281 6-OMe 3-Br F 282 6-OMe 3-Me F 283 6-OMe 3-CN F 284 6-OMe 3-NO₂ F 285 6-OMe 3-OMe F 286 6-OMe 2-F F 287 6-OMe 2-Cl F 288 6-OMe 2-Br F 289 6-OMe 2-Me F 290 6-OMe 2-CN F 291 6-OMe 2-NO₂ F 292 6-OMe 2-OMe F 293 6-OMe 2,3-F₂ F 294 6-OMe 2,4-F₂ F 295 6-OMe 2,5-F₂ F 296 6-OMe 2,6-F₂ F 297 6-OMe 3,4-F₂ F 298 6-OMe 3,5-F₂ F 299 6-OMe 2,3-Cl₂ F 300 6-OMe 2,4-Cl₂ F 301 6-OMe 2,5-Cl₂ F 302 6-OMe 2,6-Cl₂ F 303 6-OMe 3,4-Cl₂ F 304 6-OMe 3,5-Cl₂ F 305 6-OMe 2-F, 3-Cl F 306 6-OMe 2-F, 4-Cl F 307 6-OMe 2-F, 5-Cl F 308 6-OMe 2-F, 6-Cl F 309 6-OMe 2,6-F₂, 4-Cl F 310 6-OMe 3-F, 4-Cl F 311 6-OMe 3-Cl, 5-F F 312 6-OMe 2-Cl, 5-F F 313 6-OMe 3-CN, 4-Cl F 314 6-OMe 3-NO₂, 4-Cl F 315 6-OMe 2-F, 4-Br F 316 2-F 4-F F 317 2-F 4-Cl F 318 2-F 4-Br F 319 2-F H F 320 2-F 4-Me F 321 2-F 4-CN F 322 2-F 4-NO₂ F 323 2-F 4-OMe F 324 2-F 3-F F 325 2-F 3-Cl F 326 2-F 3-Br F 327 2-F 3-Me F 328 2-F 3-CN F 329 2-F 3-NO₂ F 330 2-F 3-OMe F 331 2-F 2-F F 332 2-F 2-Cl F 333 2-F 2-Br F 334 2-F 2-Me F 335 2-F 2-CN F 336 2-F 2-NO₂ F 337 2-F 2-OMe F 338 2-F 2,3-F₂ F 339 2-F 2,4-F₂ F 340 2-F 2,5-F₂ F 341 2-F 2,6-F₂ F 342 2-F 3,4-F₂ F 343 2-F 3,5-F₂ F 344 2-F 2,3-Cl₂ F 345 2-F 2,4-Cl₂ F 346 2-F 2,5-Cl₂ F 347 2-F 2,6-Cl₂ F 348 2-F 3,4-Cl₂ F 349 2-F 3,5-Cl₂ F 350 2-F 2-F, 3-Cl F 351 2-F 2-F, 4-Cl F 352 2-F 2-F, 5-Cl F 353 2-F 2-F, 6-Cl F 354 2-F 2,6-F₂, 4-Cl F 355 2-F 3-F, 4-Cl F 356 2-F 3-Cl, 5-F F 357 2-F 2-Cl, 5-F F 358 2-F 3-CN, 4-Cl F 359 2-F 3-NO₂, 4-Cl F 360 2-F 2-F, 4-Br F 361 4-F 4-F F 362 4-F 4-Cl F 363 4-F 4-Br F 364 4-F H F 365 4-F 4-Me F 366 4-F 4-CN F 367 4-F 4-NO₂ F 368 4-F 4-OMe F 369 4-F 3-F F 370 4-F 3-Cl F 371 4-F 3-Br F 372 4-F 3-Me F 373 4-F 3-CN F 374 4-F 3-NO₂ F 375 4-F 3-OMe F 376 4-F 2-F F 377 4-F 2-Cl F 378 4-F 2-Br F 379 4-F 2-Me F 380 4-F 2-CN F 381 4-F 2-NO₂ F 382 4-F 2-OMe F 383 4-F 2,3-F₂ F 384 4-F 2,4-F₂ F 385 4-F 2,5-F₂ F 386 4-F 2,6-F₂ F 387 4-F 3,4-F₂ F 388 4-F 3,5-F₂ F 389 4-F 2,3-Cl₂ F 390 4-F 2,4-Cl₂ F 391 4-F 2,5-Cl₂ F 392 4-F 2,6-Cl₂ F 393 4-F 3,4-Cl₂ F 394 4-F 3,5-Cl₂ F 395 4-F 2-F, 3-Cl F 396 4-F 2-F, 4-Cl F 397 4-F 2-F, 5-Cl F 398 4-F 2-F, 6-Cl F 399 4-F 2,6-F₂, 4-Cl F 400 4-F 3-F, 4-Cl F 401 4-F 3-Cl, 5-F F 402 4-F 2-Cl, 5-F F 403 4-F 3-CN, 4-Cl F 404 4-F 3-NO₂, 4-Cl F 405 4-F 2-F, 4-Br F 406 2-Cl 4-F F 407 2-Cl 4-Cl F 408 2-Cl 4-Br F 409 2-Cl H F 410 2-Cl 4-Me F 411 2-Cl 4-CN F 412 2-Cl 4-NO₂ F 413 2-Cl 4-OMe F 414 2-Cl 3-F F 415 2-Cl 3-Cl F 416 2-Cl 3-Br F 417 2-Cl 3-Me F 418 2-Cl 3-CN F 419 2-Cl 3-NO₂ F 420 2-Cl 3-OMe F 421 2-Cl 2-F F 422 2-Cl 2-Cl F 423 2-Cl 2-Br F 424 2-Cl 2-Me F 425 2-Cl 2-CN F 426 2-Cl 2-NO₂ F 427 2-Cl 2-OMe F 428 2-Cl 2,3-F₂ F 429 2-Cl 2,4-F₂ F 430 2-Cl 2,5-F₂ F 431 2-Cl 2,6-F₂ F 432 2-Cl 3,4-F₂ F 433 2-Cl 3,5-F₂ F 434 2-Cl 2,3-Cl₂ F 435 2-Cl 2,4-Cl₂ F 436 2-Cl 2,5-Cl₂ F 437 2-Cl 2,6-Cl₂ F 438 2-Cl 3,4-Cl₂ F 439 2-Cl 3,5-Cl₂ F 440 2-Cl 2-F, 3-Cl F 441 2-Cl 2-F, 4-Cl F 442 2-Cl 2-F, 5-Cl F 443 2-Cl 2-F, 6-Cl F 444 2-Cl 2,6-F₂, 4-Cl F 445 2-Cl 3-F, 4-Cl F 446 2-Cl 3-Cl, 5-F F 447 2-Cl 2-Cl, 5-F F 448 2-Cl 3-CN, 4-Cl F 449 2-Cl 3-NO₂, 4-Cl F 450 2-Cl 2-F, 4-Br F 451 4-Cl 4-F F 452 4-Cl 4-Cl F 453 4-Cl 4-Br F 454 4-Cl H F 455 4-Cl 4-Me F 456 4-Cl 4-CN F 457 4-Cl 4-NO₂ F 458 4-Cl 4-OMe F 459 4-Cl 3-F F 460 4-Cl 3-Cl F 461 4-Cl 3-Br F 462 4-Cl 3-Me F 463 4-Cl 3-CN F 464 4-Cl 3-NO₂ F 465 4-Cl 3-OMe F 466 4-Cl 2-F F 467 4-Cl 2-Cl F 468 4-Cl 2-Br F 469 4-Cl 2-Me F 470 4-Cl 2-CN F 471 4-Cl 2-NO₂ F 472 4-Cl 2-OMe F 473 4-Cl 2,3-F₂ F 474 4-Cl 2,4-F₂ F 475 4-Cl 2,5-F₂ F 476 4-Cl 2,6-F₂ F 477 4-Cl 3,4-F₂ F 478 4-Cl 3,5-F₂ F 479 4-Cl 2,3-Cl₂ F 480 4-Cl 2,4-Cl₂ F 481 4-Cl 2,5-Cl₂ F 482 4-Cl 2,6-Cl₂ F 483 4-Cl 3,4-Cl₂ F 484 4-Cl 3,5-Cl₂ F 485 4-Cl 2-F, 3-Cl F 486 4-Cl 2-F, 4-Cl F 487 4-Cl 2-F, 5-Cl F 488 4-Cl 2-F, 6-Cl F 489 4-Cl 2,6-F₂, 4-Cl F 490 4-Cl 3-F, 4-Cl F 491 4-Cl 3-Cl, 5-F F 492 4-Cl 2-Cl, 5-F F 493 4-Cl 3-CN, 4-Cl F 494 4-Cl 3-NO₂, 4-Cl F 495 4-Cl 2-F, 4-Br F 496 6-OCF₂H 4-F F 497 6-OCF₂H 4-Cl F 498 6-OCF₂H 4-Br F 499 6-OCF₂H H F 500 6-OCF₂H 4-Me F 501 6-OCF₂H 4-CN F 502 6-OCF₂H 4-NO₂ F 503 6-OCF₂H 4-OMe F 504 6-OCF₂H 3-F F 505 6-OCF₂H 3-Cl F 506 6-OCF₂H 3-Br F 507 6-OCF₂H 3-Me F 508 6-OCF₂H 3-CN F 509 6-OCF₂H 3-NO₂ F 510 6-OCF₂H 3-OMe F 511 6-OCF₂H 2-F F 512 6-OCF₂H 2-Cl F 513 6-OCF₂H 2-Br F 514 6-OCF₂H 2-Me F 515 6-OCF₂H 2-CN F 516 6-OCF₂H 2-NO₂ F 517 6-OCF₂H 2-OMe F 518 6-OCF₂H 2,3-F₂ F 519 6-OCF₂H 2,4-F₂ F 520 6-OCF₂H 2,5-F₂ F 521 6-OCF₂H 2,6-F₂ F 522 6-OCF₂H 3,4-F₂ F 523 6-OCF₂H 3,5-F₂ F 524 6-OCF₂H 2,3-Cl₂ F 525 6-OCF₂H 2,4-Cl₂ F 526 6-OCF₂H 2,5-Cl₂ F 527 6-OCF₂H 2,6-Cl₂ F 528 6-OCF₂H 3,4-Cl₂ F 529 6-OCF₂H 3,5-Cl₂ F 530 6-OCF₂H 2-F, 3-Cl F 531 6-OCF₂H 2-F, 4-Cl F 532 6-OCF₂H 2-F, 5-Cl F 533 6-OCF₂H 2-F, 6-Cl F 534 6-OCF₂H 2,6-F₂, 4-Cl F 535 6-OCF₂H 3-F, 4-Cl F 536 6-OCF₂H 3-Cl, 5-F F 537 6-OCF₂H 2-Cl, 5-F F 538 6-OCF₂H 3-CN, 4-Cl F 539 6-OCF₂H 3-NO₂, 4-Cl F 540 6-OCF₂H 2-F, 4-Br F 541 H 4-F Cl 542 H 4-Cl Cl 543 H 4-Br Cl 544 H H Cl 545 H 4-Me Cl 546 H 4-CN Cl 547 H 4-NO₂ Cl 548 H 4-OMe Cl 549 H 3-F Cl 550 H 3-Cl Cl 551 H 3-Br Cl 552 H 3-Me Cl 553 H 3-CN Cl 554 H 3-NO₂ Cl 555 H 3-OMe Cl 556 H 2-F Cl 557 H 2-Cl Cl 558 H 2-Br Cl 559 H 2-Me Cl 560 H 2-CN Cl 561 H 2-NO₂ Cl 562 H 2-OMe Cl 563 H 2,3-F₂ Cl 564 H 2,4-F₂ Cl 565 H 2,5-F₂ Cl 566 H 2,6-F₂ Cl 567 H 3,4-F₂ Cl 568 H 3,5-F₂ Cl 569 H 2,3-Cl₂ Cl 570 H 2,4-Cl₂ Cl 571 H 2,5-Cl₂ Cl 572 H 2,6-Cl₂ Cl 573 H 3,4-Cl₂ Cl 574 H 3,5-Cl₂ Cl 575 H 2-F, 3-Cl Cl 576 H 2-F, 4-Cl Cl 577 H 2-F, 5-Cl Cl 578 H 2-F, 6-Cl Cl 579 H 2,6-F₂, 4-Cl Cl 580 H 3-F, 4-Cl Cl 581 H 3-Cl, 5-F Cl 582 H 2-Cl, 5-F Cl 583 H 3-CN, 4-Cl Cl 584 H 3-NO₂, 4-Cl Cl 585 H 2-F, 4-Br Cl 586 6-F 4-F Cl 587 6-F 4-Cl Cl 588 6-F 4-Br Cl 589 6-F H Cl 590 6-F 4-Me Cl 591 6-F 4-CN Cl 592 6-F 4-NO₂ Cl 593 6-F 4-OMe Cl 594 6-F 3-F Cl 595 6-F 3-Cl Cl 596 6-F 3-Br Cl 597 6-F 3-Me Cl 598 6-F 3-CN Cl 599 6-F 3-NO₂ Cl 600 6-F 3-OMe Cl 601 6-F 2-F Cl 602 6-F 2-Cl Cl 603 6-F 2-Br Cl 604 6-F 2-Me Cl 605 6-F 2-CN Cl 606 6-F 2-NO₂ Cl 607 6-F 2-OMe Cl 608 6-F 2,3-F₂ Cl 609 6-F 2,4-F₂ Cl 610 6-F 2,5-F₂ Cl 611 6-F 2,6-F₂ Cl 612 6-F 3,4-F₂ Cl 613 6-F 3,5-F₂ Cl 614 6-F 2,3-Cl₂ Cl 615 6-F 2,4-Cl₂ Cl 616 6-F 2,5-Cl₂ Cl 617 6-F 2,6-Cl₂ Cl 618 6-F 3,4-Cl₂ Cl 619 6-F 3,5-Cl₂ Cl 620 6-F 2-F, 3-Cl Cl 621 6-F 2-F, 4-Cl Cl 622 6-F 2-F, 5-Cl Cl 623 6-F 2-F, 6-Cl Cl 624 6-F 2,6-F₂, 4-Cl Cl 625 6-F 3-F, 4-Cl Cl 626 6-F 3-Cl, 5-F Cl 627 6-F 2-Cl, 5-F Cl 628 6-F 3-CN, 4-Cl Cl 629 6-F 3-NO₂, 4-Cl Cl 630 6-F 2-F, 4-Br Cl 631 6-Cl 4-F Cl 632 6-Cl 4-Cl Cl 633 6-Cl 4-Br Cl 634 6-Cl H Cl 635 6-Cl 4-Me Cl 636 6-Cl 4-CN Cl 637 6-Cl 4-NO₂ Cl 638 6-Cl 4-OMe Cl 639 6-Cl 3-F Cl 640 6-Cl 3-Cl Cl 641 6-Cl 3-Br Cl 642 6-Cl 3-Me Cl 643 6-Cl 3-CN Cl 644 6-Cl 3-NO₂ Cl 645 6-Cl 3-OMe Cl 646 6-Cl 2-F Cl 647 6-Cl 2-Cl Cl 648 6-Cl 2-Br Cl 649 6-Cl 2-Me Cl 650 6-Cl 2-CN Cl 651 6-Cl 2-NO₂ Cl 652 6-Cl 2-OMe Cl 653 6-Cl 2,3-F₂ Cl 654 6-Cl 2,4-F₂ Cl 655 6-Cl 2,5-F₂ Cl 656 6-Cl 2,6-F₂ Cl 657 6-Cl 3,4-F₂ Cl 658 6-Cl 3,5-F₂ Cl 659 6-Cl 2,3-Cl₂ Cl 660 6-Cl 2,4-Cl₂ Cl 661 6-Cl 2,5-Cl₂ Cl 662 6-Cl 2,6-Cl₂ Cl 663 6-Cl 3,4-Cl₂ Cl 664 6-Cl 3,5-Cl₂ Cl 665 6-Cl 2-F, 3-Cl Cl 666 6-Cl 2-F, 4-Cl Cl 667 6-Cl 2-F, 5-Cl Cl 668 6-Cl 2-F, 6-Cl Cl 669 6-Cl 2,6-F₂, 4-Cl Cl 670 6-Cl 3-F, 4-Cl Cl 671 6-Cl 3-Cl, 5-F Cl 672 6-Cl 2-Cl, 5-F Cl 673 6-Cl 3-CN, 4-Cl Cl 674 6-Cl 3-NO₂, 4-Cl Cl 675 6-Cl 2-F, 4-Br Cl 676 6-Br 4-F Cl 677 6-Br 4-Cl Cl 678 6-Br 4-Br Cl 679 6-Br H Cl 680 6-Br 4-Me Cl 681 6-Br 4-CN Cl 682 6-Br 4-NO₂ Cl 683 6-Br 4-OMe Cl 684 6-Br 3-F Cl 685 6-Br 3-Cl Cl 686 6-Br 3-Br Cl 687 6-Br 3-Me Cl 688 6-Br 3-CN Cl 689 6-Br 3-NO₂ Cl 690 6-Br 3-OMe Cl 691 6-Br 2-F Cl 692 6-Br 2-Cl Cl 693 6-Br 2-Br Cl 694 6-Br 2-Me Cl 695 6-Br 2-CN Cl 696 6-Br 2-NO₂ Cl 697 6-Br 2-OMe Cl 698 6-Br 2,3-F₂ Cl 699 6-Br 2,4-F₂ Cl 700 6-Br 2,5-F₂ Cl 701 6-Br 2,6-F₂ Cl 702 6-Br 3,4-F₂ Cl 703 6-Br 3,5-F₂ Cl 704 6-Br 2,3-Cl₂ Cl 705 6-Br 2,4-Cl₂ Cl 706 6-Br 2,5-Cl₂ Cl 707 6-Br 2,6-Cl₂ Cl 708 6-Br 3,4-Cl₂ Cl 709 6-Br 3,5-Cl₂ Cl 710 6-Br 2-F, 3-Cl Cl 711 6-Br 2-F, 4-Cl Cl 712 6-Br 2-F, 5-Cl Cl 713 6-Br 2-F, 6-Cl Cl 714 6-Br 2,6-F₂, 4-Cl Cl 715 6-Br 3-F, 4-Cl Cl 716 6-Br 3-Cl, 5-F Cl 717 6-Br 2-Cl, 5-F Cl 718 6-Br 3-CN, 4-Cl Cl 719 6-Br 3-NO₂, 4-Cl Cl 720 6-Br 2-F, 4-Br Cl 721 6-CN 4-F Cl 722 6-CN 4-Cl Cl 723 6-CN 4-Br Cl 724 6-CN H Cl 725 6-CN 4-Me Cl 726 6-CN 4-CN Cl 727 6-CN 4-NO₂ Cl 728 6-CN 4-OMe Cl 729 6-CN 3-F Cl 730 6-CN 3-Cl Cl 731 6-CN 3-Br Cl 732 6-CN 3-Me Cl 733 6-CN 3-CN Cl 734 6-CN 3-NO₂ Cl 735 6-CN 3-OMe Cl 736 6-CN 2-F Cl 737 6-CN 2-Cl Cl 738 6-CN 2-Br Cl 739 6-CN 2-Me Cl 740 6-CN 2-CN Cl 741 6-CN 2-NO₂ Cl 742 6-CN 2-OMe Cl 743 6-CN 2,3-F₂ Cl 744 6-CN 2,4-F₂ Cl 745 6-CN 2,5-F₂ Cl 746 6-CN 2,6-F₂ Cl 747 6-CN 3,4-F₂ Cl 748 6-CN 3,5-F₂ Cl 749 6-CN 2,3-Cl₂ Cl 750 6-CN 2,4-Cl₂ Cl 751 6-CN 2,5-Cl₂ Cl 752 6-CN 2,6-Cl₂ Cl 753 6-CN 3,4-Cl₂ Cl 754 6-CN 3,5-Cl₂ Cl 755 6-CN 2-F, 3-Cl Cl 756 6-CN 2-F, 4-Cl Cl 757 6-CN 2-F, 5-Cl Cl 758 6-CN 2-F, 6-Cl Cl 759 6-CN 2,6-F₂, 4-Cl Cl 760 6-CN 3-F, 4-Cl Cl 761 6-CN 3-Cl, 5-F Cl 762 6-CN 2-Cl, 5-F Cl 763 6-CN 3-CN, 4-Cl Cl 764 6-CN 3-NO₂, 4-Cl Cl 765 6-CN 2-F, 4-Br Cl 766 6-Me 4-F Cl 767 6-Me 4-Cl Cl 768 6-Me 4-Br Cl 769 6-Me H Cl 770 6-Me 4-Me Cl 771 6-Me 4-CN Cl 772 6-Me 4-NO₂ Cl 773 6-Me 4-OMe Cl 774 6-Me 3-F Cl 775 6-Me 3-Cl Cl 776 6-Me 3-Br Cl 777 6-Me 3-Me Cl 778 6-Me 3-CN Cl 779 6-Me 3-NO₂ Cl 780 6-Me 3-OMe Cl 781 6-Me 2-F Cl 782 6-Me 2-Cl Cl 783 6-Me 2-Br Cl 784 6-Me 2-Me Cl 785 6-Me 2-CN Cl 786 6-Me 2-NO₂ Cl 787 6-Me 2-OMe Cl 788 6-Me 2,3-F₂ Cl 789 6-Me 2,4-F₂ Cl 790 6-Me 2,5-F₂ Cl 791 6-Me 2,6-F₂ Cl 792 6-Me 3,4-F₂ Cl 793 6-Me 3,5-F₂ Cl 794 6-Me 2,3-Cl₂ Cl 795 6-Me 2,4-Cl₂ Cl 796 6-Me 2,5-Cl₂ Cl 797 6-Me 2,6-Cl₂ Cl 798 6-Me 3,4-Cl₂ Cl 799 6-Me 3,5-Cl₂ Cl 800 6-Me 2-F, 3-Cl Cl 801 6-Me 2-F, 4-Cl Cl 802 6-Me 2-F, 5-Cl Cl 803 6-Me 2-F, 6-Cl Cl 804 6-Me 2,6-F₂, 4-Cl Cl 805 6-Me 3-F, 4-Cl Cl 806 6-Me 3-Cl, 5-F Cl 807 6-Me 2-Cl, 5-F Cl 808 6-Me 3-CN, 4-Cl Cl 809 6-Me 3-NO₂, 4-Cl Cl 810 6-Me 2-F, 4-Br Cl 811 6-OMe 4-F Cl 812 6-OMe 4-Cl Cl 813 6-OMe 4-Br Cl 814 6-OMe H Cl 815 6-OMe 4-Me Cl 816 6-OMe 4-CN Cl 817 6-OMe 4-NO₂ Cl 818 6-OMe 4-OMe Cl 819 6-OMe 3-F Cl 820 6-OMe 3-Cl Cl 821 6-OMe 3-Br Cl 822 6-OMe 3-Me Cl 823 6-OMe 3-CN Cl 824 6-OMe 3-NO₂ Cl 825 6-OMe 3-OMe Cl 826 6-OMe 2-F Cl 827 6-OMe 2-Cl Cl 828 6-OMe 2-Br Cl 829 6-OMe 2-Me Cl 830 6-OMe 2-CN Cl 831 6-OMe 2-NO₂ Cl 832 6-OMe 2-OMe Cl 833 6-OMe 2,3-F₂ Cl 834 6-OMe 2,4-F₂ Cl 835 6-OMe 2,5-F₂ Cl 836 6-OMe 2,6-F₂ Cl 837 6-OMe 3,4-F₂ Cl 838 6-OMe 3,5-F₂ Cl 839 6-OMe 2,3-Cl₂ Cl 840 6-OMe 2,4-Cl₂ Cl 841 6-OMe 2,5-Cl₂ Cl 842 6-OMe 2,6-Cl₂ Cl 843 6-OMe 3,4-Cl₂ Cl 844 6-OMe 3,5-Cl₂ Cl 845 6-OMe 2-F, 3-Cl Cl 846 6-OMe 2-F, 4-Cl Cl 847 6-OMe 2-F, 5-Cl Cl 848 6-OMe 2-F, 6-Cl Cl 849 6-OMe 2,6-F₂, 4-Cl Cl 850 6-OMe 3-F, 4-Cl Cl 851 6-OMe 3-Cl, 5-F Cl 852 6-OMe 2-Cl, 5-F Cl 853 6-OMe 3-CN, 4-Cl Cl 854 6-OMe 3-NO₂, 4-Cl Cl 855 6-OMe 2-F, 4-Br Cl 856 2-F 4-F Cl 857 2-F 4-Cl Cl 858 2-F 4-Br Cl 859 2-F H Cl 860 2-F 4-Me Cl 861 2-F 4-CN Cl 862 2-F 4-NO₂ Cl 863 2-F 4-OMe Cl 864 2-F 3-F Cl 865 2-F 3-Cl Cl 866 2-F 3-Br Cl 867 2-F 3-Me Cl 868 2-F 3-CN Cl 869 2-F 3-NO₂ Cl 870 2-F 3-OMe Cl 871 2-F 2-F Cl 872 2-F 2-Cl Cl 873 2-F 2-Br Cl 874 2-F 2-Me Cl 875 2-F 2-CN Cl 876 2-F 2-NO₂ Cl 877 2-F 2-OMe Cl 878 2-F 2,3-F₂ Cl 879 2-F 2,4-F₂ Cl 880 2-F 2,5-F₂ Cl 881 2-F 2,6-F₂ Cl 882 2-F 3,4-F₂ Cl 883 2-F 3,5-F₂ Cl 884 2-F 2,3-Cl₂ Cl 885 2-F 2,4-Cl₂ Cl 886 2-F 2,5-Cl₂ Cl 887 2-F 2,6-Cl₂ Cl 888 2-F 3,4-Cl₂ Cl 889 2-F 3,5-Cl₂ Cl 890 2-F 2-F, 3-Cl Cl 891 2-F 2-F, 4-Cl Cl 892 2-F 2-F, 5-Cl Cl 893 2-F 2-F, 6-Cl Cl 894 2-F 2,6-F₂, 4-Cl Cl 895 2-F 3-F, 4-Cl Cl 896 2-F 3-Cl, 5-F Cl 897 2-F 2-Cl, 5-F Cl 898 2-F 3-CN, 4-Cl Cl 899 2-F 3-NO₂, 4-Cl Cl 900 2-F 2-F, 4-Br Cl 901 4-F 4-F Cl 902 4-F 4-Cl Cl 903 4-F 4-Br Cl 904 4-F H Cl 905 4-F 4-Me Cl 906 4-F 4-CN Cl 907 4-F 4-NO₂ Cl 908 4-F 4-OMe Cl 909 4-F 3-F Cl 910 4-F 3-Cl Cl 911 4-F 3-Br Cl 912 4-F 3-Me Cl 913 4-F 3-CN Cl 914 4-F 3-NO₂ Cl 915 4-F 3-OMe Cl 916 4-F 2-F Cl 917 4-F 2-Cl Cl 918 4-F 2-Br Cl 919 4-F 2-Me Cl 920 4-F 2-CN Cl 921 4-F 2-NO₂ Cl 922 4-F 2-OMe Cl 923 4-F 2,3-F₂ Cl 924 4-F 2,4-F₂ Cl 925 4-F 2,5-F₂ Cl 926 4-F 2,6-F₂ Cl 927 4-F 3,4-F₂ Cl 928 4-F 3,5-F₂ Cl 929 4-F 2,3-Cl₂ Cl 930 4-F 2,4-Cl₂ Cl 931 4-F 2,5-Cl₂ Cl 932 4-F 2,6-Cl₂ Cl 933 4-F 3,4-Cl₂ Cl 934 4-F 3,5-Cl₂ Cl 935 4-F 2-F, 3-Cl Cl 936 4-F 2-F, 4-Cl Cl 937 4-F 2-F, 5-Cl Cl 938 4-F 2-F, 6-Cl Cl 939 4-F 2,6-F₂, 4-Cl Cl 940 4-F 3-F, 4-Cl Cl 941 4-F 3-Cl, 5-F Cl 942 4-F 2-Cl, 5-F Cl 943 4-F 3-CN, 4-Cl Cl 944 4-F 3-NO₂, 4-Cl Cl 945 4-F 2-F, 4-Br Cl 946 2-Cl 4-F Cl 947 2-Cl 4-Cl Cl 948 2-Cl 4-Br Cl 949 2-Cl H Cl 950 2-Cl 4-Me Cl 951 2-Cl 4-CN Cl 952 2-Cl 4-NO₂ Cl 953 2-Cl 4-OMe Cl 954 2-Cl 3-F Cl 955 2-Cl 3-Cl Cl 956 2-Cl 3-Br Cl 957 2-Cl 3-Me Cl 958 2-Cl 3-CN Cl 959 2-Cl 3-NO₂ Cl 960 2-Cl 3-OMe Cl 961 2-Cl 2-F Cl 962 2-Cl 2-Cl Cl 963 2-Cl 2-Br Cl 964 2-Cl 2-Me Cl 965 2-Cl 2-CN Cl 966 2-Cl 2-NO₂ Cl 967 2-Cl 2-OMe Cl 968 2-Cl 2,3-F₂ Cl 969 2-Cl 2,4-F₂ Cl 970 2-Cl 2,5-F₂ Cl 971 2-Cl 2,6-F₂ Cl 972 2-Cl 3,4-F₂ Cl 973 2-Cl 3,5-F₂ Cl 974 2-Cl 2,3-Cl₂ Cl 975 2-Cl 2,4-Cl₂ Cl 976 2-Cl 2,5-Cl₂ Cl 977 2-Cl 2,6-Cl₂ Cl 978 2-Cl 3,4-Cl₂ Cl 979 2-Cl 3,5-Cl₂ Cl 980 2-Cl 2-F, 3-Cl Cl 981 2-Cl 2-F, 4-Cl Cl 982 2-Cl 2-F, 5-Cl Cl 983 2-Cl 2-F, 6-Cl Cl 984 2-Cl 2,6-F₂, 4-Cl Cl 985 2-Cl 3-F, 4-Cl Cl 986 2-Cl 3-Cl, 5-F Cl 987 2-Cl 2-Cl, 5-F Cl 988 2-Cl 3-CN, 4-Cl Cl 989 2-Cl 3-NO₂, 4-Cl Cl 990 2-Cl 2-F, 4-Br Cl 991 4-Cl 4-F Cl 992 4-Cl 4-Cl Cl 993 4-Cl 4-Br Cl 994 4-Cl H Cl 995 4-Cl 4-Me Cl 996 4-Cl 4-CN Cl 997 4-Cl 4-NO₂ Cl 998 4-Cl 4-OMe Cl 999 4-Cl 3-F Cl 1000 4-Cl 3-Cl Cl 1001 4-Cl 3-Br Cl 1002 4-Cl 3-Me Cl 1003 4-Cl 3-CN Cl 1004 4-Cl 3-NO₂ Cl 1005 4-Cl 3-OMe Cl 1006 4-Cl 2-F Cl 1007 4-Cl 2-Cl Cl 1008 4-Cl 2-Br Cl 1009 4-Cl 2-Me Cl 1010 4-Cl 2-CN Cl 1011 4-Cl 2-NO₂ Cl 1012 4-Cl 2-OMe Cl 1013 4-Cl 2,3-F₂ Cl 1014 4-Cl 2,4-F₂ Cl 1015 4-Cl 2,5-F₂ Cl 1016 4-Cl 2,6-F₂ Cl 1017 4-Cl 3,4-F₂ Cl 1018 4-Cl 3,5-F₂ Cl 1019 4-Cl 2,3-Cl₂ Cl 1020 4-Cl 2,4-Cl₂ Cl 1021 4-Cl 2,5-Cl₂ Cl 1022 4-Cl 2,6-Cl₂ Cl 1023 4-Cl 3,4-Cl₂ Cl 1024 4-Cl 3,5-Cl₂ Cl 1025 4-Cl 2-F, 3-Cl Cl 1026 4-Cl 2-F, 4-Cl Cl 1027 4-Cl 2-F, 5-Cl Cl 1028 4-Cl 2-F, 6-Cl Cl 1029 4-Cl 2,6-F₂, 4-Cl Cl 1030 4-Cl 3-F, 4-Cl Cl 1031 4-Cl 3-Cl, 5-F Cl 1032 4-Cl 2-Cl, 5-F Cl 1033 4-Cl 3-CN, 4-Cl Cl 1034 4-Cl 3-NO₂, 4-Cl Cl 1035 4-Cl 2-F, 4-Br Cl 1036 6-OCF₂H 4-F Cl 1037 6-OCF₂H 4-Cl Cl 1038 6-OCF₂H 4-Br Cl 1039 6-OCF₂H H Cl 1040 6-OCF₂H 4-Me Cl 1041 6-OCF₂H 4-CN Cl 1042 6-OCF₂H 4-NO₂ Cl 1043 6-OCF₂H 4-OMe Cl 1044 6-OCF₂H 3-F Cl 1045 6-OCF₂H 3-Cl Cl 1046 6-OCF₂H 3-Br Cl 1047 6-OCF₂H 3-Me Cl 1048 6-OCF₂H 3-CN Cl 1049 6-OCF₂H 3-NO₂ Cl 1050 6-OCF₂H 3-OMe Cl 1051 6-OCF₂H 2-F Cl 1052 6-OCF₂H 2-Cl Cl 1053 6-OCF₂H 2-Br Cl 1054 6-OCF₂H 2-Me Cl 1055 6-OCF₂H 2-CN Cl 1056 6-OCF₂H 2-NO₂ Cl 1057 6-OCF₂H 2-OMe Cl 1058 6-OCF₂H 2,3-F₂ Cl 1059 6-OCF₂H 2,4-F₂ Cl 1060 6-OCF₂H 2,5-F₂ Cl 1061 6-OCF₂H 2,6-F₂ Cl 1062 6-OCF₂H 3,4-F₂ Cl 1063 6-OCF₂H 3,5-F₂ Cl 1064 6-OCF₂H 2,3-Cl₂ Cl 1065 6-OCF₂H 2,4-Cl₂ Cl 1066 6-OCF₂H 2,5-Cl₂ Cl 1067 6-OCF₂H 2,6-Cl₂ Cl 1068 6-OCF₂H 3,4-Cl₂ Cl 1069 6-OCF₂H 3,5-Cl₂ Cl 1070 6-OCF₂H 2-F, 3-Cl Cl 1071 6-OCF₂H 2-F, 4-Cl Cl 1072 6-OCF₂H 2-F, 5-Cl Cl 1073 6-OCF₂H 2-F, 6-Cl Cl 1074 6-OCF₂H 2,6-F₂, 4-Cl Cl 1075 6-OCF₂H 3-F, 4-Cl Cl 1076 6-OCF₂H 3-Cl, 5-F Cl 1077 6-OCF₂H 2-Cl, 5-F Cl 1078 6-OCF₂H 3-CN, 4-Cl Cl 1079 6-OCF₂H 3-NO₂, 4-Cl Cl 1080 6-OCF₂H 2-F, 4-Br Cl 1081 H 4-F Br 1082 H 4-Cl Br 1083 H 4-Br Br 1084 H H Br 1085 H 4-Me Br 1086 H 4-CN Br 1087 H 4-NO₂ Br 1088 H 4-OMe Br 1089 H 3-F Br 1090 H 3-Cl Br 1091 H 3-Br Br 1092 H 3-Me Br 1093 H 3-CN Br 1094 H 3-NO₂ Br 1095 H 3-OMe Br 1096 H 2-F Br 1097 H 2-Cl Br 1098 H 2-Br Br 1099 H 2-Me Br 1100 H 2-CN Br 1101 H 2-NO₂ Br 1102 H 2-OMe Br 1103 H 2,3-F₂ Br 1104 H 2,4-F₂ Br 1105 H 2,5-F₂ Br 1106 H 2,6-F₂ Br 1107 H 3,4-F₂ Br 1108 H 3,5-F₂ Br 1109 H 2,3-Cl₂ Br 1110 H 2,4-Cl₂ Br 1111 H 2,5-Cl₂ Br 1112 H 2,6-Cl₂ Br 1113 H 3,4-Cl₂ Br 1114 H 3,5-Cl₂ Br 1115 H 2-F, 3-Cl Br 1116 H 2-F, 4-Cl Br 1117 H 2-F, 5-Cl Br 1118 H 2-F, 6-Cl Br 1119 H 2,6-F₂, 4-Cl Br 1120 H 3-F, 4-Cl Br 1121 H 3-Cl, 5-F Br 1122 H 2-Cl, 5-F Br 1123 H 3-CN, 4-Cl Br 1124 H 3-NO₂, 4-Cl Br 1125 H 2-F, 4-Br Br 1126 6-F 4-F Br 1127 6-F 4-Cl Br 1128 6-F 4-Br Br 1129 6-F H Br 1130 6-F 4-Me Br 1131 6-F 4-CN Br 1132 6-F 4-NO₂ Br 1133 6-F 4-OMe Br 1134 6-F 3-F Br 1135 6-F 3-Cl Br 1136 6-F 3-Br Br 1137 6-F 3-Me Br 1138 6-F 3-CN Br 1139 6-F 3-NO₂ Br 1140 6-F 3-OMe Br 1141 6-F 2-F Br 1142 6-F 2-Cl Br 1143 6-F 2-Br Br 1144 6-F 2-Me Br 1145 6-F 2-CN Br 1146 6-F 2-NO₂ Br 1147 6-F 2-OMe Br 1148 6-F 2,3-F₂ Br 1149 6-F 2,4-F₂ Br 1150 6-F 2,5-F₂ Br 1151 6-F 2,6-F₂ Br 1152 6-F 3,4-F₂ Br 1153 6-F 3,5-F₂ Br 1154 6-F 2,3-Cl₂ Br 1155 6-F 2,4-Cl₂ Br 1156 6-F 2,5-Cl₂ Br 1157 6-F 2,6-Cl₂ Br 1158 6-F 3,4-Cl₂ Br 1159 6-F 3,5-Cl₂ Br 1160 6-F 2-F, 3-Cl Br 1161 6-F 2-F, 4-Cl Br 1162 6-F 2-F, 5-Cl Br 1163 6-F 2-F, 6-Cl Br 1164 6-F 2,6-F₂, 4-Cl Br 1165 6-F 3-F, 4-Cl Br 1166 6-F 3-Cl, 5-F Br 1167 6-F 2-Cl, 5-F Br 1168 6-F 3-CN, 4-Cl Br 1169 6-F 3-NO₂, 4-Cl Br 1170 6-F 2-F, 4-Br Br 1171 6-Cl 4-F Br 1172 6-Cl 4-Cl Br 1173 6-Cl 4-Br Br 1174 6-Cl H Br 1175 6-Cl 4-Me Br 1176 6-Cl 4-CN Br 1177 6-Cl 4-NO₂ Br 1178 6-Cl 4-OMe Br 1179 6-Cl 3-F Br 1180 6-Cl 3-Cl Br 1181 6-Cl 3-Br Br 1182 6-Cl 3-Me Br 1183 6-Cl 3-CN Br 1184 6-Cl 3-NO₂ Br 1185 6-Cl 3-OMe Br 1186 6-Cl 2-F Br 1187 6-Cl 2-Cl Br 1188 6-Cl 2-Br Br 1189 6-Cl 2-Me Br 1190 6-Cl 2-CN Br 1191 6-Cl 2-NO₂ Br 1192 6-Cl 2-OMe Br 1193 6-Cl 2,3-F₂ Br 1194 6-Cl 2,4-F₂ Br 1195 6-Cl 2,5-F₂ Br 1196 6-Cl 2,6-F₂ Br 1197 6-Cl 3,4-F₂ Br 1198 6-Cl 3,5-F₂ Br 1199 6-Cl 2,3-Cl₂ Br 1200 6-Cl 2,4-Cl₂ Br 1201 6-Cl 2,5-Cl₂ Br 1202 6-Cl 2,6-Cl₂ Br 1203 6-Cl 3,4-Cl₂ Br 1204 6-Cl 3,5-Cl₂ Br 1205 6-Cl 2-F, 3-Cl Br 1206 6-Cl 2-F, 4-Cl Br 1207 6-Cl 2-F, 5-Cl Br 1208 6-Cl 2-F, 6-Cl Br 1209 6-Cl 2,6-F₂, 4-Cl Br 1210 6-Cl 3-F, 4-Cl Br 1211 6-Cl 3-Cl, 5-F Br 1212 6-Cl 2-Cl, 5-F Br 1213 6-Cl 3-CN, 4-Cl Br 1214 6-Cl 3-NO₂, 4-Cl Br 1215 6-Cl 2-F, 4-Br Br 1216 6-Br 4-F Br 1217 6-Br 4-Cl Br 1218 6-Br 4-Br Br 1219 6-Br H Br 1220 6-Br 4-Me Br 1221 6-Br 4-CN Br 1222 6-Br 4-NO₂ Br 1223 6-Br 4-OMe Br 1224 6-Br 3-F Br 1225 6-Br 3-Cl Br 1226 6-Br 3-Br Br 1227 6-Br 3-Me Br 1228 6-Br 3-CN Br 1229 6-Br 3-NO₂ Br 1230 6-Br 3-OMe Br 1231 6-Br 2-F Br 1232 6-Br 2-Cl Br 1233 6-Br 2-Br Br 1234 6-Br 2-Me Br 1235 6-Br 2-CN Br 1236 6-Br 2-NO₂ Br 1237 6-Br 2-OMe Br 1238 6-Br 2,3-F₂ Br 1239 6-Br 2,4-F₂ Br 1240 6-Br 2,5-F₂ Br 1241 6-Br 2,6-F₂ Br 1242 6-Br 3,4-F₂ Br 1243 6-Br 3,5-F₂ Br 1244 6-Br 2,3-Cl₂ Br 1245 6-Br 2,4-Cl₂ Br 1246 6-Br 2,5-Cl₂ Br 1247 6-Br 2,6-Cl₂ Br 1248 6-Br 3,4-Cl₂ Br 1249 6-Br 3,5-Cl₂ Br 1250 6-Br 2-F, 3-Cl Br 1251 6-Br 2-F, 4-Cl Br 1252 6-Br 2-F, 5-Cl Br 1253 6-Br 2-F, 6-Cl Br 1254 6-Br 2,6-F₂, 4-Cl Br 1255 6-Br 3-F, 4-Cl Br 1256 6-Br 3-Cl, 5-F Br 1257 6-Br 2-Cl, 5-F Br 1258 6-Br 3-CN, 4-Cl Br 1259 6-Br 3-NO₂, 4-Cl Br 1260 6-Br 2-F, 4-Br Br 1261 6-CN 4-F Br 1262 6-CN 4-Cl Br 1263 6-CN 4-Br Br 1264 6-CN H Br 1265 6-CN 4-Me Br 1266 6-CN 4-CN Br 1267 6-CN 4-NO₂ Br 1268 6-CN 4-OMe Br 1269 6-CN 3-F Br 1270 6-CN 3-Cl Br 1271 6-CN 3-Br Br 1272 6-CN 3-Me Br 1273 6-CN 3-CN Br 1274 6-CN 3-NO₂ Br 1275 6-CN 3-OMe Br 1276 6-CN 2-F Br 1277 6-CN 2-Cl Br 1278 6-CN 2-Br Br 1279 6-CN 2-Me Br 1280 6-CN 2-CN Br 1281 6-CN 2-NO₂ Br 1282 6-CN 2-OMe Br 1283 6-CN 2,3-F₂ Br 1284 6-CN 2,4-F₂ Br 1285 6-CN 2,5-F₂ Br 1286 6-CN 2,6-F₂ Br 1287 6-CN 3,4-F₂ Br 1288 6-CN 3,5-F₂ Br 1289 6-CN 2,3-Cl₂ Br 1290 6-CN 2,4-Cl₂ Br 1291 6-CN 2,5-Cl₂ Br 1292 6-CN 2,6-Cl₂ Br 1293 6-CN 3,4-Cl₂ Br 1294 6-CN 3,5-Cl₂ Br 1295 6-CN 2-F, 3-Cl Br 1296 6-CN 2-F, 4-Cl Br 1297 6-CN 2-F, 5-Cl Br 1298 6-CN 2-F, 6-Cl Br 1299 6-CN 2,6-F₂, 4-Cl Br 1300 6-CN 3-F, 4-Cl Br 1301 6-CN 3-Cl, 5-F Br 1302 6-CN 2-Cl, 5-F Br 1303 6-CN 3-CN, 4-Cl Br 1304 6-CN 3-NO₂, 4-Cl Br 1305 6-CN 2-F, 4-Br Br 1306 6-Me 4-F Br 1307 6-Me 4-Cl Br 1308 6-Me 4-Br Br 1309 6-Me H Br 1310 6-Me 4-Me Br 1311 6-Me 4-CN Br 1312 6-Me 4-NO₂ Br 1313 6-Me 4-OMe Br 1314 6-Me 3-F Br 1315 6-Me 3-Cl Br 1316 6-Me 3-Br Br 1317 6-Me 3-Me Br 1318 6-Me 3-CN Br 1319 6-Me 3-NO₂ Br 1320 6-Me 3-OMe Br 1321 6-Me 2-F Br 1322 6-Me 2-Cl Br 1323 6-Me 2-Br Br 1324 6-Me 2-Me Br 1325 6-Me 2-CN Br 1326 6-Me 2-NO₂ Br 1327 6-Me 2-OMe Br 1328 6-Me 2,3-F₂ Br 1329 6-Me 2,4-F₂ Br 1330 6-Me 2,5-F₂ Br 1331 6-Me 2,6-F₂ Br 1332 6-Me 3,4-F₂ Br 1333 6-Me 3,5-F₂ Br 1334 6-Me 2,3-Cl₂ Br 1335 6-Me 2,4-Cl₂ Br 1336 6-Me 2,5-Cl₂ Br 1337 6-Me 2,6-Cl₂ Br 1338 6-Me 3,4-Cl₂ Br 1339 6-Me 3,5-Cl₂ Br 1340 6-Me 2-F, 3-Cl Br 1341 6-Me 2-F, 4-Cl Br 1342 6-Me 2-F, 5-Cl Br 1343 6-Me 2-F, 6-Cl Br 1344 6-Me 2,6-F₂, 4-Cl Br 1345 6-Me 3-F, 4-Cl Br 1346 6-Me 3-Cl, 5-F Br 1347 6-Me 2-Cl, 5-F Br 1348 6-Me 3-CN, 4-Cl Br 1349 6-Me 3-NO₂, 4-Cl Br 1350 6-Me 2-F, 4-Br Br 1351 6-OMe 4-F Br 1352 6-OMe 4-Cl Br 1353 6-OMe 4-Br Br 1354 6-OMe H Br 1355 6-OMe 4-Me Br 1356 6-OMe 4-CN Br 1357 6-OMe 4-NO₂ Br 1358 6-OMe 4-OMe Br 1359 6-OMe 3-F Br 1360 6-OMe 3-Cl Br 1361 6-OMe 3-Br Br 1362 6-OMe 3-Me Br 1363 6-OMe 3-CN Br 1364 6-OMe 3-NO₂ Br 1365 6-OMe 3-OMe Br 1366 6-OMe 2-F Br 1367 6-OMe 2-Cl Br 1368 6-OMe 2-Br Br 1369 6-OMe 2-Me Br 1370 6-OMe 2-CN Br 1371 6-OMe 2-NO₂ Br 1372 6-OMe 2-OMe Br 1373 6-OMe 2,3-F₂ Br 1374 6-OMe 2,4-F₂ Br 1375 6-OMe 2,5-F₂ Br 1376 6-OMe 2,6-F₂ Br 1377 6-OMe 3,4-F₂ Br 1378 6-OMe 3,5-F₂ Br 1379 6-OMe 2,3-Cl₂ Br 1380 6-OMe 2,4-Cl₂ Br 1381 6-OMe 2,5-Cl₂ Br 1382 6-OMe 2,6-Cl₂ Br 1383 6-OMe 3,4-Cl₂ Br 1384 6-OMe 3,5-Cl₂ Br 1385 6-OMe 2-F, 3-Cl Br 1386 6-OMe 2-F, 4-Cl Br 1387 6-OMe 2-F, 5-Cl Br 1388 6-OMe 2-F, 6-Cl Br 1389 6-OMe 2,6-F₂, 4-Cl Br 1390 6-OMe 3-F, 4-Cl Br 1391 6-OMe 3-Cl, 5-F Br 1392 6-OMe 2-Cl, 5-F Br 1393 6-OMe 3-CN, 4-Cl Br 1394 6-OMe 3-NO₂, 4-Cl Br 1395 6-OMe 2-F, 4-Br Br 1396 2-F 4-F Br 1397 2-F 4-Cl Br 1398 2-F 4-Br Br 1399 2-F H Br 1400 2-F 4-Me Br 1401 2-F 4-CN Br 1402 2-F 4-NO₂ Br 1403 2-F 4-OMe Br 1404 2-F 3-F Br 1405 2-F 3-Cl Br 1406 2-F 3-Br Br 1407 2-F 3-Me Br 1408 2-F 3-CN Br 1409 2-F 3-NO₂ Br 1410 2-F 3-OMe Br 1411 2-F 2-F Br 1412 2-F 2-Cl Br 1413 2-F 2-Br Br 1414 2-F 2-Me Br 1415 2-F 2-CN Br 1416 2-F 2-NO₂ Br 1417 2-F 2-OMe Br 1418 2-F 2,3-F₂ Br 1419 2-F 2,4-F₂ Br 1420 2-F 2,5-F₂ Br 1421 2-F 2,6-F₂ Br 1422 2-F 3,4-F₂ Br 1423 2-F 3,5-F₂ Br 1424 2-F 2,3-Cl₂ Br 1425 2-F 2,4-Cl₂ Br 1426 2-F 2,5-Cl₂ Br 1427 2-F 2,6-Cl₂ Br 1428 2-F 3,4-Cl₂ Br 1429 2-F 3,5-Cl₂ Br 1430 2-F 2-F, 3-Cl Br 1431 2-F 2-F, 4-Cl Br 1432 2-F 2-F, 5-Cl Br 1433 2-F 2-F, 6-Cl Br 1434 2-F 2,6-F₂, 4-Cl Br 1435 2-F 3-F, 4-Cl Br 1436 2-F 3-Cl, 5-F Br 1437 2-F 2-Cl, 5-F Br 1438 2-F 3-CN, 4-Cl Br 1439 2-F 3-NO₂, 4-Cl Br 1440 2-F 2-F, 4-Br Br 1441 4-F 4-F Br 1442 4-F 4-Cl Br 1443 4-F 4-Br Br 1444 4-F H Br 1445 4-F 4-Me Br 1446 4-F 4-CN Br 1447 4-F 4-NO₂ Br 1448 4-F 4-OMe Br 1449 4-F 3-F Br 1450 4-F 3-Cl Br 1451 4-F 3-Br Br 1452 4-F 3-Me Br 1453 4-F 3-CN Br 1454 4-F 3-NO₂ Br 1455 4-F 3-OMe Br 1456 4-F 2-F Br 1457 4-F 2-Cl Br 1458 4-F 2-Br Br 1459 4-F 2-Me Br 1460 4-F 2-CN Br 1461 4-F 2-NO₂ Br 1462 4-F 2-OMe Br 1463 4-F 2,3-F₂ Br 1464 4-F 2,4-F₂ Br 1465 4-F 2,5-F₂ Br 1466 4-F 2,6-F₂ Br 1467 4-F 3,4-F₂ Br 1468 4-F 3,5-F₂ Br 1469 4-F 2,3-Cl₂ Br 1470 4-F 2,4-Cl₂ Br 1471 4-F 2,5-Cl₂ Br 1472 4-F 2,6-Cl₂ Br 1473 4-F 3,4-Cl₂ Br 1474 4-F 3,5-Cl₂ Br 1475 4-F 2-F, 3-Cl Br 1476 4-F 2-F, 4-Cl Br 1477 4-F 2-F, 5-Cl Br 1478 4-F 2-F, 6-Cl Br 1479 4-F 2,6-F₂, 4-Cl Br 1480 4-F 3-F, 4-Cl Br 1481 4-F 3-Cl, 5-F Br 1482 4-F 2-Cl, 5-F Br 1483 4-F 3-CN, 4-Cl Br 1484 4-F 3-NO₂, 4-Cl Br 1485 4-F 2-F, 4-Br Br 1486 2-Cl 4-F Br 1487 2-Cl 4-Cl Br 1488 2-Cl 4-Br Br 1489 2-Cl H Br 1490 2-Cl 4-Me Br 1491 2-Cl 4-CN Br 1492 2-Cl 4-NO₂ Br 1493 2-Cl 4-OMe Br 1494 2-Cl 3-F Br 1495 2-Cl 3-Cl Br 1496 2-Cl 3-Br Br 1497 2-Cl 3-Me Br 1498 2-Cl 3-CN Br 1499 2-Cl 3-NO₂ Br 1500 2-Cl 3-OMe Br 1501 2-Cl 2-F Br 1502 2-Cl 2-Cl Br 1503 2-Cl 2-Br Br 1504 2-Cl 2-Me Br 1505 2-Cl 2-CN Br 1506 2-Cl 2-NO₂ Br 1507 2-Cl 2-OMe Br 1508 2-Cl 2,3-F₂ Br 1509 2-Cl 2,4-F₂ Br 1510 2-Cl 2,5-F₂ Br 1511 2-Cl 2,6-F₂ Br 1512 2-Cl 3,4-F₂ Br 1513 2-Cl 3,5-F₂ Br 1514 2-Cl 2,3-Cl₂ Br 1515 2-Cl 2,4-Cl₂ Br 1516 2-Cl 2,5-Cl₂ Br 1517 2-Cl 2,6-Cl₂ Br 1518 2-Cl 3,4-Cl₂ Br 1519 2-Cl 3,5-Cl₂ Br 1520 2-Cl 2-F, 3-Cl Br 1521 2-Cl 2-F, 4-Cl Br 1522 2-Cl 2-F, 5-Cl Br 1523 2-Cl 2-F, 6-Cl Br 1524 2-Cl 2,6-F₂, 4-Cl Br 1525 2-Cl 3-F, 4-Cl Br 1526 2-Cl 3-Cl, 5-F Br 1527 2-Cl 2-Cl, 5-F Br 1528 2-Cl 3-CN, 4-Cl Br 1529 2-Cl 3-NO₂, 4-Cl Br 1530 2-Cl 2-F, 4-Br Br 1531 4-Cl 4-F Br 1532 4-Cl 4-Cl Br 1533 4-Cl 4-Br Br 1534 4-Cl H Br 1535 4-Cl 4-Me Br 1536 4-Cl 4-CN Br 1537 4-Cl 4-NO₂ Br 1538 4-Cl 4-OMe Br 1539 4-Cl 3-F Br 1540 4-Cl 3-Cl Br 1541 4-Cl 3-Br Br 1542 4-Cl 3-Me Br 1543 4-Cl 3-CN Br 1544 4-Cl 3-NO₂ Br 1545 4-Cl 3-OMe Br 1546 4-Cl 2-F Br 1547 4-Cl 2-Cl Br 1548 4-Cl 2-Br Br 1549 4-Cl 2-Me Br 1550 4-Cl 2-CN Br 1551 4-Cl 2-NO₂ Br 1552 4-Cl 2-OMe Br 1553 4-Cl 2,3-F₂ Br 1554 4-Cl 2,4-F₂ Br 1555 4-Cl 2,5-F₂ Br 1556 4-Cl 2,6-F₂ Br 1557 4-Cl 3,4-F₂ Br 1558 4-Cl 3,5-F₂ Br 1559 4-Cl 2,3-Cl₂ Br 1560 4-Cl 2,4-Cl₂ Br 1561 4-Cl 2,5-Cl₂ Br 1562 4-Cl 2,6-Cl₂ Br 1563 4-Cl 3,4-Cl₂ Br 1564 4-Cl 3,5-Cl₂ Br 1565 4-Cl 2-F, 3-Cl Br 1566 4-Cl 2-F, 4-Cl Br 1567 4-Cl 2-F, 5-Cl Br 1568 4-Cl 2-F, 6-Cl Br 1569 4-Cl 2,6-F₂, 4-Cl Br 1570 4-Cl 3-F, 4-Cl Br 1571 4-Cl 3-Cl, 5-F Br 1572 4-Cl 2-Cl, 5-F Br 1573 4-Cl 3-CN, 4-Cl Br 1574 4-Cl 3-NO₂, 4-Cl Br 1575 4-Cl 2-F, 4-Br Br 1576 6-OCF₂H 4-F Br 1577 6-OCF₂H 4-Cl Br 1578 6-OCF₂H 4-Br Br 1579 6-OCF₂H H Br 1580 6-OCF₂H 4-Me Br 1581 6-OCF₂H 4-CN Br 1582 6-OCF₂H 4-NO₂ Br 1583 6-OCF₂H 4-OMe Br 1584 6-OCF₂H 3-F Br 1585 6-OCF₂H 3-Cl Br 1586 6-OCF₂H 3-Br Br 1587 6-OCF₂H 3-Me Br 1588 6-OCF₂H 3-CN Br 1589 6-OCF₂H 3-NO₂ Br 1590 6-OCF₂H 3-OMe Br 1591 6-OCF₂H 2-F Br 1592 6-OCF₂H 2-Cl Br 1593 6-OCF₂H 2-Br Br 1594 6-OCF₂H 2-Me Br 1595 6-OCF₂H 2-CN Br 1596 6-OCF₂H 2-NO₂ Br 1597 6-OCF₂H 2-OMe Br 1598 6-OCF₂H 2,3-F₂ Br 1599 6-OCF₂H 2,4-F₂ Br 1600 6-OCF₂H 2,5-F₂ Br 1601 6-OCF₂H 2,6-F₂ Br 1602 6-OCF₂H 3,4-F₂ Br 1603 6-OCF₂H 3,5-F₂ Br 1604 6-OCF₂H 2,3-Cl₂ Br 1605 6-OCF₂H 2,4-Cl₂ Br 1606 6-OCF₂H 2,5-Cl₂ Br 1607 6-OCF₂H 2,6-Cl₂ Br 1608 6-OCF₂H 3,4-Cl₂ Br 1609 6-OCF₂H 3,5-Cl₂ Br 1610 6-OCF₂H 2-F, 3-Cl Br 1611 6-OCF₂H 2-F, 4-Cl Br 1612 6-OCF₂H 2-F, 5-Cl Br 1613 6-OCF₂H 2-F, 6-Cl Br 1614 6-OCF₂H 2,6-F₂, 4-Cl Br 1615 6-OCF₂H 3-F, 4-Cl Br 1616 6-OCF₂H 3-Cl, 5-F Br 1617 6-OCF₂H 2-Cl, 5-F Br 1618 6-OCF₂H 3-CN, 4-Cl Br 1619 6-OCF₂H 3-NO₂, 4-Cl Br 1620 6-OCF₂H 2-F, 4-Br Br 1621 H 4-F Me 1622 H 4-Cl Me 1623 H 4-Br Me 1624 H H Me 1625 H 4-Me Me 1626 H 4-CN Me 1627 H 4-NO₂ Me 1628 H 4-OMe Me 1629 H 3-F Me 1630 H 3-Cl Me 1631 H 3-Br Me 1632 H 3-Me Me 1633 H 3-CN Me 1634 H 3-NO₂ Me 1635 H 3-OMe Me 1636 H 2-F Me 1637 H 2-Cl Me 1638 H 2-Br Me 1639 H 2-Me Me 1640 H 2-CN Me 1641 H 2-NO₂ Me 1642 H 2-OMe Me 1643 H 2,3-F₂ Me 1644 H 2,4-F₂ Me 1645 H 2,5-F₂ Me 1646 H 2,6-F₂ Me 1647 H 3,4-F₂ Me 1648 H 3,5-F₂ Me 1649 H 2,3-Cl₂ Me 1650 H 2,4-Cl₂ Me 1651 H 2,5-Cl₂ Me 1652 H 2,6-Cl₂ Me 1653 H 3,4-Cl₂ Me 1654 H 3,5-Cl₂ Me 1655 H 2-F, 3-Cl Me 1656 H 2-F, 4-Cl Me 1657 H 2-F, 5-Cl Me 1658 H 2-F, 6-Cl Me 1659 H 2,6-F₂, 4-Cl Me 1660 H 3-F, 4-Cl Me 1661 H 3-Cl, 5-F Me 1662 H 2-Cl, 5-F Me 1663 H 3-CN, 4-Cl Me 1664 H 3-NO₂, 4-Cl Me 1665 H 2-F, 4-Br Me 1666 6-F 4-F Me 1667 6-F 4-Cl Me 1668 6-F 4-Br Me 1669 6-F H Me 1670 6-F 4-Me Me 1671 6-F 4-CN Me 1672 6-F 4-NO₂ Me 1673 6-F 4-OMe Me 1674 6-F 3-F Me 1675 6-F 3-Cl Me 1676 6-F 3-Br Me 1677 6-F 3-Me Me 1678 6-F 3-CN Me 1679 6-F 3-NO₂ Me 1680 6-F 3-OMe Me 1681 6-F 2-F Me 1682 6-F 2-Cl Me 1683 6-F 2-Br Me 1684 6-F 2-Me Me 1685 6-F 2-CN Me 1686 6-F 2-NO₂ Me 1687 6-F 2-OMe Me 1688 6-F 2,3-F₂ Me 1689 6-F 2,4-F₂ Me 1690 6-F 2,5-F₂ Me 1691 6-F 2,6-F₂ Me 1692 6-F 3,4-F₂ Me 1693 6-F 3,5-F₂ Me 1694 6-F 2,3-Cl₂ Me 1695 6-F 2,4-Cl₂ Me 1696 6-F 2,5-Cl₂ Me 1697 6-F 2,6-Cl₂ Me 1698 6-F 3,4-Cl₂ Me 1699 6-F 3,5-Cl₂ Me 1700 6-F 2-F, 3-Cl Me 1701 6-F 2-F, 4-Cl Me 1702 6-F 2-F, 5-Cl Me 1703 6-F 2-F, 6-Cl Me 1704 6-F 2,6-F₂, 4-Cl Me 1705 6-F 3-F, 4-Cl Me 1706 6-F 3-Cl, 5-F Me 1707 6-F 2-Cl, 5-F Me 1708 6-F 3-CN, 4-Cl Me 1709 6-F 3-NO₂, 4-Cl Me 1710 6-F 2-F, 4-Br Me 1711 6-Cl 4-F Me 1712 6-Cl 4-Cl Me 1713 6-Cl 4-Br Me 1714 6-Cl H Me 1715 6-Cl 4-Me Me 1716 6-Cl 4-CN Me 1717 6-Cl 4-NO₂ Me 1718 6-Cl 4-OMe Me 1719 6-Cl 3-F Me 1720 6-Cl 3-Cl Me 1721 6-Cl 3-Br Me 1722 6-Cl 3-Me Me 1723 6-Cl 3-CN Me 1724 6-Cl 3-NO₂ Me 1725 6-Cl 3-OMe Me 1726 6-Cl 2-F Me 1727 6-Cl 2-Cl Me 1728 6-Cl 2-Br Me 1729 6-Cl 2-Me Me 1730 6-Cl 2-CN Me 1731 6-Cl 2-NO₂ Me 1732 6-Cl 2-OMe Me 1733 6-Cl 2,3-F₂ Me 1734 6-Cl 2,4-F₂ Me 1735 6-Cl 2,5-F₂ Me 1736 6-Cl 2,6-F₂ Me 1737 6-Cl 3,4-F₂ Me 1738 6-Cl 3,5-F₂ Me 1739 6-Cl 2,3-Cl₂ Me 1740 6-Cl 2,4-Cl₂ Me 1741 6-Cl 2,5-Cl₂ Me 1742 6-Cl 2,6-Cl₂ Me 1743 6-Cl 3,4-Cl₂ Me 1744 6-Cl 3,5-Cl₂ Me 1745 6-Cl 2-F, 3-Cl Me 1746 6-Cl 2-F, 4-Cl Me 1747 6-Cl 2-F, 5-Cl Me 1748 6-Cl 2-F, 6-Cl Me 1749 6-Cl 2,6-F₂, 4-Cl Me 1750 6-Cl 3-F, 4-Cl Me 1751 6-Cl 3-Cl, 5-F Me 1752 6-Cl 2-Cl, 5-F Me 1753 6-Cl 3-CN, 4-Cl Me 1754 6-Cl 3-NO₂, 4-Cl Me 1755 6-Cl 2-F, 4-Br Me 1756 6-Br 4-F Me 1757 6-Br 4-Cl Me 1758 6-Br 4-Br Me 1759 6-Br H Me 1760 6-Br 4-Me Me 1761 6-Br 4-CN Me 1762 6-Br 4-NO₂ Me 1763 6-Br 4-OMe Me 1764 6-Br 3-F Me 1765 6-Br 3-Cl Me 1766 6-Br 3-Br Me 1767 6-Br 3-Me Me 1768 6-Br 3-CN Me 1769 6-Br 3-NO₂ Me 1770 6-Br 3-OMe Me 1771 6-Br 2-F Me 1772 6-Br 2-Cl Me 1773 6-Br 2-Br Me 1774 6-Br 2-Me Me 1775 6-Br 2-CN Me 1776 6-Br 2-NO₂ Me 1777 6-Br 2-OMe Me 1778 6-Br 2,3-F₂ Me 1779 6-Br 2,4-F₂ Me 1780 6-Br 2,5-F₂ Me 1781 6-Br 2,6-F₂ Me 1782 6-Br 3,4-F₂ Me 1783 6-Br 3,5-F₂ Me 1784 6-Br 2,3-Cl₂ Me 1785 6-Br 2,4-Cl₂ Me 1786 6-Br 2,5-Cl₂ Me 1787 6-Br 2,6-Cl₂ Me 1788 6-Br 3,4-Cl₂ Me 1789 6-Br 3,5-Cl₂ Me 1790 6-Br 2-F, 3-Cl Me 1791 6-Br 2-F, 4-Cl Me 1792 6-Br 2-F, 5-Cl Me 1793 6-Br 2-F, 6-Cl Me 1794 6-Br 2,6-F₂, 4-Cl Me 1795 6-Br 3-F, 4-Cl Me 1796 6-Br 3-Cl, 5-F Me 1797 6-Br 2-Cl, 5-F Me 1798 6-Br 3-CN, 4-Cl Me 1799 6-Br 3-NO₂, 4-Cl Me 1800 6-Br 2-F, 4-Br Me 1801 6-CN 4-F Me 1802 6-CN 4-Cl Me 1803 6-CN 4-Br Me 1804 6-CN H Me 1805 6-CN 4-Me Me 1806 6-CN 4-CN Me 1807 6-CN 4-NO₂ Me 1808 6-CN 4-OMe Me 1809 6-CN 3-F Me 1810 6-CN 3-Cl Me 1811 6-CN 3-Br Me 1812 6-CN 3-Me Me 1813 6-CN 3-CN Me 1814 6-CN 3-NO₂ Me 1815 6-CN 3-OMe Me 1816 6-CN 2-F Me 1817 6-CN 2-Cl Me 1818 6-CN 2-Br Me 1819 6-CN 2-Me Me 1820 6-CN 2-CN Me 1821 6-CN 2-NO₂ Me 1822 6-CN 2-OMe Me 1823 6-CN 2,3-F₂ Me 1824 6-CN 2,4-F₂ Me 1825 6-CN 2,5-F₂ Me 1826 6-CN 2,6-F₂ Me 1827 6-CN 3,4-F₂ Me 1828 6-CN 3,5-F₂ Me 1829 6-CN 2,3-Cl₂ Me 1830 6-CN 2,4-Cl₂ Me 1831 6-CN 2,5-Cl₂ Me 1832 6-CN 2,6-Cl₂ Me 1833 6-CN 3,4-Cl₂ Me 1834 6-CN 3,5-Cl₂ Me 1835 6-CN 2-F, 3-Cl Me 1836 6-CN 2-F, 4-Cl Me 1837 6-CN 2-F, 5-Cl Me 1838 6-CN 2-F, 6-Cl Me 1839 6-CN 2,6-F₂, 4-Cl Me 1840 6-CN 3-F, 4-Cl Me 1841 6-CN 3-Cl, 5-F Me 1842 6-CN 2-Cl, 5-F Me 1843 6-CN 3-CN, 4-Cl Me 1844 6-CN 3-NO₂, 4-Cl Me 1845 6-CN 2-F, 4-Br Me 1846 6-Me 4-F Me 1847 6-Me 4-Cl Me 1848 6-Me 4-Br Me 1849 6-Me H Me 1850 6-Me 4-Me Me 1851 6-Me 4-CN Me 1852 6-Me 4-NO₂ Me 1853 6-Me 4-OMe Me 1854 6-Me 3-F Me 1855 6-Me 3-Cl Me 1856 6-Me 3-Br Me 1857 6-Me 3-Me Me 1858 6-Me 3-CN Me 1859 6-Me 3-NO₂ Me 1860 6-Me 3-OMe Me 1861 6-Me 2-F Me 1862 6-Me 2-Cl Me 1863 6-Me 2-Br Me 1864 6-Me 2-Me Me 1865 6-Me 2-CN Me 1866 6-Me 2-NO₂ Me 1867 6-Me 2-OMe Me 1868 6-Me 2,3-F₂ Me 1869 6-Me 2,4-F₂ Me 1870 6-Me 2,5-F₂ Me 1871 6-Me 2,6-F₂ Me 1872 6-Me 3,4-F₂ Me 1873 6-Me 3,5-F₂ Me 1874 6-Me 2,3-Cl₂ Me 1875 6-Me 2,4-Cl₂ Me 1876 6-Me 2,5-Cl₂ Me 1877 6-Me 2,6-Cl₂ Me 1878 6-Me 3,4-Cl₂ Me 1879 6-Me 3,5-Cl₂ Me 1880 6-Me 2-F, 3-Cl Me 1881 6-Me 2-F, 4-Cl Me 1882 6-Me 2-F, 5-Cl Me 1883 6-Me 2-F, 6-Cl Me 1884 6-Me 2,6-F₂, 4-Cl Me 1885 6-Me 3-F, 4-Cl Me 1886 6-Me 3-Cl, 5-F Me 1887 6-Me 2-Cl, 5-F Me 1888 6-Me 3-CN, 4-Cl Me 1889 6-Me 3-NO₂, 4-Cl Me 1890 6-Me 2-F, 4-Br Me 1891 6-OMe 4-F Me 1892 6-OMe 4-Cl Me 1893 6-OMe 4-Br Me 1894 6-OMe H Me 1895 6-OMe 4-Me Me 1896 6-OMe 4-CN Me 1897 6-OMe 4-NO₂ Me 1898 6-OMe 4-OMe Me 1899 6-OMe 3-F Me 1900 6-OMe 3-Cl Me 1901 6-OMe 3-Br Me 1902 6-OMe 3-Me Me 1903 6-OMe 3-CN Me 1904 6-OMe 3-NO₂ Me 1905 6-OMe 3-OMe Me 1906 6-OMe 2-F Me 1907 6-OMe 2-Cl Me 1908 6-OMe 2-Br Me 1909 6-OMe 2-Me Me 1910 6-OMe 2-CN Me 1911 6-OMe 2-NO₂ Me 1912 6-OMe 2-OMe Me 1913 6-OMe 2,3-F₂ Me 1914 6-OMe 2,4-F₂ Me 1915 6-OMe 2,5-F₂ Me 1916 6-OMe 2,6-F₂ Me 1917 6-OMe 3,4-F₂ Me 1918 6-OMe 3,5-F₂ Me 1919 6-OMe 2,3-Cl₂ Me 1920 6-OMe 2,4-Cl₂ Me 1921 6-OMe 2,5-Cl₂ Me 1922 6-OMe 2,6-Cl₂ Me 1923 6-OMe 3,4-Cl₂ Me 1924 6-OMe 3,5-Cl₂ Me 1925 6-OMe 2-F, 3-Cl Me 1926 6-OMe 2-F, 4-Cl Me 1927 6-OMe 2-F, 5-Cl Me 1928 6-OMe 2-F, 6-Cl Me 1929 6-OMe 2,6-F₂, 4-Cl Me 1930 6-OMe 3-F, 4-Cl Me 1931 6-OMe 3-Cl, 5-F Me 1932 6-OMe 2-Cl, 5-F Me 1933 6-OMe 3-CN, 4-Cl Me 1934 6-OMe 3-NO₂, 4-Cl Me 1935 6-OMe 2-F, 4-Br Me 1936 2-F 4-F Me 1937 2-F 4-Cl Me 1938 2-F 4-Br Me 1939 2-F H Me 1940 2-F 4-Me Me 1941 2-F 4-CN Me 1942 2-F 4-NO₂ Me 1943 2-F 4-OMe Me 1944 2-F 3-F Me 1945 2-F 3-Cl Me 1946 2-F 3-Br Me 1947 2-F 3-Me Me 1948 2-F 3-CN Me 1949 2-F 3-NO₂ Me 1950 2-F 3-OMe Me 1951 2-F 2-F Me 1952 2-F 2-Cl Me 1953 2-F 2-Br Me 1954 2-F 2-Me Me 1955 2-F 2-CN Me 1956 2-F 2-NO₂ Me 1957 2-F 2-OMe Me 1958 2-F 2,3-F₂ Me 1959 2-F 2,4-F₂ Me 1960 2-F 2,5-F₂ Me 1961 2-F 2,6-F₂ Me 1962 2-F 3,4-F₂ Me 1963 2-F 3,5-F₂ Me 1964 2-F 2,3-Cl₂ Me 1965 2-F 2,4-Cl₂ Me 1966 2-F 2,5-Cl₂ Me 1967 2-F 2,6-Cl₂ Me 1968 2-F 3,4-Cl₂ Me 1969 2-F 3,5-Cl₂ Me 1970 2-F 2-F, 3-Cl Me 1971 2-F 2-F, 4-Cl Me 1972 2-F 2-F, 5-Cl Me 1973 2-F 2-F, 6-Cl Me 1974 2-F 2,6-F₂, 4-Cl Me 1975 2-F 3-F, 4-Cl Me 1976 2-F 3-Cl, 5-F Me 1977 2-F 2-Cl, 5-F Me 1978 2-F 3-CN, 4-Cl Me 1979 2-F 3-NO₂, 4-Cl Me 1980 2-F 2-F, 4-Br Me 1981 4-F 4-F Me 1982 4-F 4-Cl Me 1983 4-F 4-Br Me 1984 4-F H Me 1985 4-F 4-Me Me 1986 4-F 4-CN Me 1987 4-F 4-NO₂ Me 1988 4-F 4-OMe Me 1989 4-F 3-F Me 1990 4-F 3-Cl Me 1991 4-F 3-Br Me 1992 4-F 3-Me Me 1993 4-F 3-CN Me 1994 4-F 3-NO₂ Me 1995 4-F 3-OMe Me 1996 4-F 2-F Me 1997 4-F 2-Cl Me 1998 4-F 2-Br Me 1999 4-F 2-Me Me 2000 4-F 2-CN Me 2001 4-F 2-NO₂ Me 2002 4-F 2-OMe Me 2003 4-F 2,3-F₂ Me 2004 4-F 2,4-F₂ Me 2005 4-F 2,5-F₂ Me 2006 4-F 2,6-F₂ Me 2007 4-F 3,4-F₂ Me 2008 4-F 3,5-F₂ Me 2009 4-F 2,3-Cl₂ Me 2010 4-F 2,4-Cl₂ Me 2011 4-F 2,5-Cl₂ Me 2012 4-F 2,6-Cl₂ Me 2013 4-F 3,4-Cl₂ Me 2014 4-F 3,5-Cl₂ Me 2015 4-F 2-F, 3-Cl Me 2016 4-F 2-F, 4-Cl Me 2017 4-F 2-F, 5-Cl Me 2018 4-F 2-F, 6-Cl Me 2019 4-F 2,6-F₂, 4-Cl Me 2020 4-F 3-F, 4-Cl Me 2021 4-F 3-Cl, 5-F Me 2022 4-F 2-Cl, 5-F Me 2023 4-F 3-CN, 4-Cl Me 2024 4-F 3-NO₂, 4-Cl Me 2025 4-F 2-F, 4-Br Me 2026 2-Cl 4-F Me 2027 2-Cl 4-Cl Me 2028 2-Cl 4-Br Me 2029 2-Cl H Me 2030 2-Cl 4-Me Me 2031 2-Cl 4-CN Me 2032 2-Cl 4-NO₂ Me 2033 2-Cl 4-OMe Me 2034 2-Cl 3-F Me 2035 2-Cl 3-Cl Me 2036 2-Cl 3-Br Me 2037 2-Cl 3-Me Me 2038 2-Cl 3-CN Me 2039 2-Cl 3-NO₂ Me 2040 2-Cl 3-OMe Me 2041 2-Cl 2-F Me 2042 2-Cl 2-Cl Me 2043 2-Cl 2-Br Me 2044 2-Cl 2-Me Me 2045 2-Cl 2-CN Me 2046 2-Cl 2-NO₂ Me 2047 2-Cl 2-OMe Me 2048 2-Cl 2,3-F₂ Me 2049 2-Cl 2,4-F₂ Me 2050 2-Cl 2,5-F₂ Me 2051 2-Cl 2,6-F₂ Me 2052 2-Cl 3,4-F₂ Me 2053 2-Cl 3,5-F₂ Me 2054 2-Cl 2,3-Cl₂ Me 2055 2-Cl 2,4-Cl₂ Me 2056 2-Cl 2,5-Cl₂ Me 2057 2-Cl 2,6-Cl₂ Me 2058 2-Cl 3,4-Cl₂ Me 2059 2-Cl 3,5-Cl₂ Me 2060 2-Cl 2-F, 3-Cl Me 2061 2-Cl 2-F, 4-Cl Me 2062 2-Cl 2-F, 5-Cl Me 2063 2-Cl 2-F, 6-Cl Me 2064 2-Cl 2,6-F₂, 4-Cl Me 2065 2-Cl 3-F, 4-Cl Me 2066 2-Cl 3-Cl, 5-F Me 2067 2-Cl 2-Cl, 5-F Me 2068 2-Cl 3-CN, 4-Cl Me 2069 2-Cl 3-NO₂, 4-Cl Me 2070 2-Cl 2-F, 4-Br Me 2071 4-Cl 4-F Me 2072 4-Cl 4-Cl Me 2073 4-Cl 4-Br Me 2074 4-Cl H Me 2075 4-Cl 4-Me Me 2076 4-Cl 4-CN Me 2077 4-Cl 4-NO₂ Me 2078 4-Cl 4-OMe Me 2079 4-Cl 3-F Me 2080 4-Cl 3-Cl Me 2081 4-Cl 3-Br Me 2082 4-Cl 3-Me Me 2083 4-Cl 3-CN Me 2084 4-Cl 3-NO₂ Me 2085 4-Cl 3-OMe Me 2086 4-Cl 2-F Me 2087 4-Cl 2-Cl Me 2088 4-Cl 2-Br Me 2089 4-Cl 2-Me Me 2090 4-Cl 2-CN Me 2091 4-Cl 2-NO₂ Me 2092 4-Cl 2-OMe Me 2093 4-Cl 2,3-F₂ Me 2094 4-Cl 2,4-F₂ Me 2095 4-Cl 2,5-F₂ Me 2096 4-Cl 2,6-F₂ Me 2097 4-Cl 3,4-F₂ Me 2098 4-Cl 3,5-F₂ Me 2099 4-Cl 2,3-Cl₂ Me 2100 4-Cl 2,4-Cl₂ Me 2101 4-Cl 2,5-Cl₂ Me 2102 4-Cl 2,6-Cl₂ Me 2103 4-Cl 3,4-Cl₂ Me 2104 4-Cl 3,5-Cl₂ Me 2105 4-Cl 2-F, 3-Cl Me 2106 4-Cl 2-F, 4-Cl Me 2107 4-Cl 2-F, 5-Cl Me 2108 4-Cl 2-F, 6-Cl Me 2109 4-Cl 2,6-F₂, 4-Cl Me 2110 4-Cl 3-F, 4-Cl Me 2111 4-Cl 3-Cl, 5-F Me 2112 4-Cl 2-Cl, 5-F Me 2113 4-Cl 3-CN, 4-Cl Me 2114 4-Cl 3-NO₂, 4-Cl Me 2115 4-Cl 2-F, 4-Br Me 2116 6-OCF₂H 4-F Me 2117 6-OCF₂H 4-Cl Me 2118 6-OCF₂H 4-Br Me 2119 6-OCF₂H H Me 2120 6-OCF₂H 4-Me Me 2121 6-OCF₂H 4-CN Me 2122 6-OCF₂H 4-NO₂ Me 2123 6-OCF₂H 4-OMe Me 2124 6-OCF₂H 3-F Me 2125 6-OCF₂H 3-Cl Me 2126 6-OCF₂H 3-Br Me 2127 6-OCF₂H 3-Me Me 2128 6-OCF₂H 3-CN Me 2129 6-OCF₂H 3-NO₂ Me 2130 6-OCF₂H 3-OMe Me 2131 6-OCF₂H 2-F Me 2132 6-OCF₂H 2-Cl Me 2133 6-OCF₂H 2-Br Me 2134 6-OCF₂H 2-Me Me 2135 6-OCF₂H 2-CN Me 2136 6-OCF₂H 2-NO₂ Me 2137 6-OCF₂H 2-OMe Me 2138 6-OCF₂H 2,3-F₂ Me 2139 6-OCF₂H 2,4-F₂ Me 2140 6-OCF₂H 2,5-F₂ Me 2141 6-OCF₂H 2,6-F₂ Me 2142 6-OCF₂H 3,4-F₂ Me 2143 6-OCF₂H 3,5-F₂ Me 2144 6-OCF₂H 2,3-Cl₂ Me 2145 6-OCF₂H 2,4-Cl₂ Me 2146 6-OCF₂H 2,5-Cl₂ Me 2147 6-OCF₂H 2,6-Cl₂ Me 2148 6-OCF₂H 3,4-Cl₂ Me 2149 6-OCF₂H 3,5-Cl₂ Me 2150 6-OCF₂H 2-F, 3-Cl Me 2151 6-OCF₂H 2-F, 4-Cl Me 2152 6-OCF₂H 2-F, 5-Cl Me 2153 6-OCF₂H 2-F, 6-Cl Me 2154 6-OCF₂H 2,6-F₂, 4-Cl Me 2155 6-OCF₂H 3-F, 4-Cl Me 2156 6-OCF₂H 3-Cl, 5-F Me 2157 6-OCF₂H 2-Cl, 5-F Me 2158 6-OCF₂H 3-CN, 4-Cl Me 2159 6-OCF₂H 3-NO₂, 4-Cl Me 2160 6-OCF₂H 2-F, 4-Br Me 2161 H 4-F CN 2162 H 4-Cl CN 2163 H 4-Br CN 2164 H H CN 2165 H 4-Me CN 2166 H 4-CN CN 2167 H 4-NO₂ CN 2168 H 4-OMe CN 2169 H 3-F CN 2170 H 3-Cl CN 2171 H 3-Br CN 2172 H 3-Me CN 2173 H 3-CN CN 2174 H 3-NO₂ CN 2175 H 3-OMe CN 2176 H 2-F CN 2177 H 2-Cl CN 2178 H 2-Br CN 2179 H 2-Me CN 2180 H 2-CN CN 2181 H 2-NO₂ CN 2182 H 2-OMe CN 2183 H 2,3-F₂ CN 2184 H 2,4-F₂ CN 2185 H 2,5-F₂ CN 2186 H 2,6-F₂ CN 2187 H 3,4-F₂ CN 2188 H 3,5-F₂ CN 2189 H 2,3-Cl₂ CN 2190 H 2,4-Cl₂ CN 2191 H 2,5-Cl₂ CN 2192 H 2,6-Cl₂ CN 2193 H 3,4-Cl₂ CN 2194 H 3,5-Cl₂ CN 2195 H 2-F, 3-Cl CN 2196 H 2-F, 4-Cl CN 2197 H 2-F, 5-Cl CN 2198 H 2-F, 6-Cl CN 2199 H 2,6-F₂, 4-Cl CN 2200 H 3-F, 4-Cl CN 2201 H 3-Cl, 5-F CN 2202 H 2-Cl, 5-F CN 2203 H 3-CN, 4-Cl CN 2204 H 3-NO₂, 4-Cl CN 2205 H 2-F, 4-Br CN 2206 6-F 4-F CN 2207 6-F 4-Cl CN 2208 6-F 4-Br CN 2209 6-F H CN 2210 6-F 4-Me CN 2211 6-F 4-CN CN 2212 6-F 4-NO₂ CN 2213 6-F 4-OMe CN 2214 6-F 3-F CN 2215 6-F 3-Cl CN 2216 6-F 3-Br CN 2217 6-F 3-Me CN 2218 6-F 3-CN CN 2219 6-F 3-NO₂ CN 2220 6-F 3-OMe CN 2221 6-F 2-F CN 2222 6-F 2-Cl CN 2223 6-F 2-Br CN 2224 6-F 2-Me CN 2225 6-F 2-CN CN 2226 6-F 2-NO₂ CN 2227 6-F 2-OMe CN 2228 6-F 2,3-F₂ CN 2229 6-F 2,4-F₂ CN 2230 6-F 2,5-F₂ CN 2231 6-F 2,6-F₂ CN 2232 6-F 3,4-F₂ CN 2233 6-F 3,5-F₂ CN 2234 6-F 2,3-Cl₂ CN 2235 6-F 2,4-Cl₂ CN 2236 6-F 2,5-Cl₂ CN 2237 6-F 2,6-Cl₂ CN 2238 6-F 3,4-Cl₂ CN 2239 6-F 3,5-Cl₂ CN 2240 6-F 2-F, 3-Cl CN 2241 6-F 2-F, 4-Cl CN 2242 6-F 2-F, 5-Cl CN 2243 6-F 2-F, 6-Cl CN 2244 6-F 2,6-F₂, 4-Cl CN 2245 6-F 3-F, 4-Cl CN 2246 6-F 3-Cl, 5-F CN 2247 6-F 2-Cl, 5-F CN 2248 6-F 3-CN, 4-Cl CN 2249 6-F 3-NO₂, 4-Cl CN 2250 6-F 2-F, 4-Br CN 2251 6-Cl 4-F CN 2252 6-Cl 4-Cl CN 2253 6-Cl 4-Br CN 2254 6-Cl H CN 2255 6-Cl 4-Me CN 2256 6-Cl 4-CN CN 2257 6-Cl 4-NO₂ CN 2258 6-Cl 4-OMe CN 2259 6-Cl 3-F CN 2260 6-Cl 3-Cl CN 2261 6-Cl 3-Br CN 2262 6-Cl 3-Me CN 2263 6-Cl 3-CN CN 2264 6-Cl 3-NO₂ CN 2265 6-Cl 3-OMe CN 2266 6-Cl 2-F CN 2267 6-Cl 2-Cl CN 2268 6-Cl 2-Br CN 2269 6-Cl 2-Me CN 2270 6-Cl 2-CN CN 2271 6-Cl 2-NO₂ CN 2272 6-Cl 2-OMe CN 2273 6-Cl 2,3-F₂ CN 2274 6-Cl 2,4-F₂ CN 2275 6-Cl 2,5-F₂ CN 2276 6-Cl 2,6-F₂ CN 2277 6-Cl 3,4-F₂ CN 2278 6-Cl 3,5-F₂ CN 2279 6-Cl 2,3-Cl₂ CN 2280 6-Cl 2,4-Cl₂ CN 2281 6-Cl 2,5-Cl₂ CN 2282 6-Cl 2,6-Cl₂ CN 2283 6-Cl 3,4-Cl₂ CN 2284 6-Cl 3,5-Cl₂ CN 2285 6-Cl 2-F, 3-Cl CN 2286 6-Cl 2-F, 4-Cl CN 2287 6-Cl 2-F, 5-Cl CN 2288 6-Cl 2-F, 6-Cl CN 2289 6-Cl 2,6-F₂, 4-Cl CN 2290 6-Cl 3-F, 4-Cl CN 2291 6-Cl 3-Cl, 5-F CN 2292 6-Cl 2-Cl, 5-F CN 2293 6-Cl 3-CN, 4-Cl CN 2294 6-Cl 3-NO₂, 4-Cl CN 2295 6-Cl 2-F, 4-Br CN 2296 6-Br 4-F CN 2297 6-Br 4-Cl CN 2298 6-Br 4-Br CN 2299 6-Br H CN 2300 6-Br 4-Me CN 2301 6-Br 4-CN CN 2302 6-Br 4-NO₂ CN 2303 6-Br 4-OMe CN 2304 6-Br 3-F CN 2305 6-Br 3-Cl CN 2306 6-Br 3-Br CN 2307 6-Br 3-Me CN 2308 6-Br 3-CN CN 2309 6-Br 3-NO₂ CN 2310 6-Br 3-OMe CN 2311 6-Br 2-F CN 2312 6-Br 2-Cl CN 2313 6-Br 2-Br CN 2314 6-Br 2-Me CN 2315 6-Br 2-CN CN 2316 6-Br 2-NO₂ CN 2317 6-Br 2-OMe CN 2318 6-Br 2,3-F₂ CN 2319 6-Br 2,4-F₂ CN 2320 6-Br 2,5-F₂ CN 2321 6-Br 2,6-F₂ CN 2322 6-Br 3,4-F₂ CN 2323 6-Br 3,5-F₂ CN 2324 6-Br 2,3-Cl₂ CN 2325 6-Br 2,4-Cl₂ CN 2326 6-Br 2,5-Cl₂ CN 2327 6-Br 2,6-Cl₂ CN 2328 6-Br 3,4-Cl₂ CN 2329 6-Br 3,5-Cl₂ CN 2330 6-Br 2-F, 3-Cl CN 2331 6-Br 2-F, 4-Cl CN 2332 6-Br 2-F, 5-Cl CN 2333 6-Br 2-F, 6-Cl CN 2334 6-Br 2,6-F₂, 4-Cl CN 2335 6-Br 3-F, 4-Cl CN 2336 6-Br 3-Cl, 5-F CN 2337 6-Br 2-Cl, 5-F CN 2338 6-Br 3-CN, 4-Cl CN 2339 6-Br 3-NO₂, 4-Cl CN 2340 6-Br 2-F, 4-Br CN 2341 6-CN 4-F CN 2342 6-CN 4-Cl CN 2343 6-CN 4-Br CN 2344 6-CN H CN 2345 6-CN 4-Me CN 2346 6-CN 4-CN CN 2347 6-CN 4-NO₂ CN 2348 6-CN 4-OMe CN 2349 6-CN 3-F CN 2350 6-CN 3-Cl CN 2351 6-CN 3-Br CN 2352 6-CN 3-Me CN 2353 6-CN 3-CN CN 2354 6-CN 3-NO₂ CN 2355 6-CN 3-OMe CN 2356 6-CN 2-F CN 2357 6-CN 2-Cl CN 2358 6-CN 2-Br CN 2359 6-CN 2-Me CN 2360 6-CN 2-CN CN 2361 6-CN 2-NO₂ CN 2362 6-CN 2-OMe CN 2363 6-CN 2,3-F₂ CN 2364 6-CN 2,4-F₂ CN 2365 6-CN 2,5-F₂ CN 2366 6-CN 2,6-F₂ CN 2367 6-CN 3,4-F₂ CN 2368 6-CN 3,5-F₂ CN 2369 6-CN 2,3-Cl₂ CN 2370 6-CN 2,4-Cl₂ CN 2371 6-CN 2,5-Cl₂ CN 2372 6-CN 2,6-Cl₂ CN 2373 6-CN 3,4-Cl₂ CN 2374 6-CN 3,5-Cl₂ CN 2375 6-CN 2-F, 3-Cl CN 2376 6-CN 2-F, 4-Cl CN 2377 6-CN 2-F, 5-Cl CN 2378 6-CN 2-F, 6-Cl CN 2379 6-CN 2,6-F₂, 4-Cl CN 2380 6-CN 3-F, 4-Cl CN 2381 6-CN 3-Cl, 5-F CN 2382 6-CN 2-Cl, 5-F CN 2383 6-CN 3-CN, 4-Cl CN 2384 6-CN 3-NO₂, 4-Cl CN 2385 6-CN 2-F, 4-Br CN 2386 6-Me 4-F CN 2387 6-Me 4-Cl CN 2388 6-Me 4-Br CN 2389 6-Me H CN 2390 6-Me 4-Me CN 2391 6-Me 4-CN CN 2392 6-Me 4-NO₂ CN 2393 6-Me 4-OMe CN 2394 6-Me 3-F CN 2395 6-Me 3-Cl CN 2396 6-Me 3-Br CN 2397 6-Me 3-Me CN 2398 6-Me 3-CN CN 2399 6-Me 3-NO₂ CN 2400 6-Me 3-OMe CN 2401 6-Me 2-F CN 2402 6-Me 2-Cl CN 2403 6-Me 2-Br CN 2404 6-Me 2-Me CN 2405 6-Me 2-CN CN 2406 6-Me 2-NO₂ CN 2407 6-Me 2-OMe CN 2408 6-Me 2,3-F₂ CN 2409 6-Me 2,4-F₂ CN 2410 6-Me 2,5-F₂ CN 2411 6-Me 2,6-F₂ CN 2412 6-Me 3,4-F₂ CN 2413 6-Me 3,5-F₂ CN 2414 6-Me 2,3-Cl₂ CN 2415 6-Me 2,4-Cl₂ CN 2416 6-Me 2,5-Cl₂ CN 2417 6-Me 2,6-Cl₂ CN 2418 6-Me 3,4-Cl₂ CN 2419 6-Me 3,5-Cl₂ CN 2420 6-Me 2-F, 3-Cl CN 2421 6-Me 2-F, 4-Cl CN 2422 6-Me 2-F, 5-Cl CN 2423 6-Me 2-F, 6-Cl CN 2424 6-Me 2,6-F₂, 4-Cl CN 2425 6-Me 3-F, 4-Cl CN 2426 6-Me 3-Cl, 5-F CN 2427 6-Me 2-Cl, 5-F CN 2428 6-Me 3-CN, 4-Cl CN 2429 6-Me 3-NO₂, 4-Cl CN 2430 6-Me 2-F, 4-Br CN 2431 6-OMe 4-F CN 2432 6-OMe 4-Cl CN 2433 6-OMe 4-Br CN 2434 6-OMe H CN 2435 6-OMe 4-Me CN 2436 6-OMe 4-CN CN 2437 6-OMe 4-NO₂ CN 2438 6-OMe 4-OMe CN 2439 6-OMe 3-F CN 2440 6-OMe 3-Cl CN 2441 6-OMe 3-Br CN 2442 6-OMe 3-Me CN 2443 6-OMe 3-CN CN 2444 6-OMe 3-NO₂ CN 2445 6-OMe 3-OMe CN 2446 6-OMe 2-F CN 2447 6-OMe 2-Cl CN 2448 6-OMe 2-Br CN 2449 6-OMe 2-Me CN 2450 6-OMe 2-CN CN 2451 6-OMe 2-NO₂ CN 2452 6-OMe 2-OMe CN 2453 6-OMe 2,3-F₂ CN 2454 6-OMe 2,4-F₂ CN 2455 6-OMe 2,5-F₂ CN 2456 6-OMe 2,6-F₂ CN 2457 6-OMe 3,4-F₂ CN 2458 6-OMe 3,5-F₂ CN 2459 6-OMe 2,3-Cl₂ CN 2460 6-OMe 2,4-Cl₂ CN 2461 6-OMe 2,5-Cl₂ CN 2462 6-OMe 2,6-Cl₂ CN 2463 6-OMe 3,4-Cl₂ CN 2464 6-OMe 3,5-Cl₂ CN 2465 6-OMe 2-F, 3-Cl CN 2466 6-OMe 2-F, 4-Cl CN 2467 6-OMe 2-F, 5-Cl CN 2468 6-OMe 2-F, 6-Cl CN 2469 6-OMe 2,6-F₂, 4-Cl CN 2470 6-OMe 3-F, 4-Cl CN 2471 6-OMe 3-Cl, 5-F CN 2472 6-OMe 2-Cl, 5-F CN 2473 6-OMe 3-CN, 4-Cl CN 2474 6-OMe 3-NO₂, 4-Cl CN 2475 6-OMe 2-F, 4-Br CN 2476 2-F 4-F CN 2477 2-F 4-Cl CN 2478 2-F 4-Br CN 2479 2-F H CN 2480 2-F 4-Me CN 2481 2-F 4-CN CN 2482 2-F 4-NO₂ CN 2483 2-F 4-OMe CN 2484 2-F 3-F CN 2485 2-F 3-Cl CN 2486 2-F 3-Br CN 2487 2-F 3-Me CN 2488 2-F 3-CN CN 2489 2-F 3-NO₂ CN 2490 2-F 3-OMe CN 2491 2-F 2-F CN 2492 2-F 2-Cl CN 2493 2-F 2-Br CN 2494 2-F 2-Me CN 2495 2-F 2-CN CN 2496 2-F 2-NO₂ CN 2497 2-F 2-OMe CN 2498 2-F 2,3-F₂ CN 2499 2-F 2,4-F₂ CN 2500 2-F 2,5-F₂ CN 2501 2-F 2,6-F₂ CN 2502 2-F 3,4-F₂ CN 2503 2-F 3,5-F₂ CN 2504 2-F 2,3-Cl₂ CN 2505 2-F 2,4-Cl₂ CN 2506 2-F 2,5-Cl₂ CN 2507 2-F 2,6-Cl₂ CN 2508 2-F 3,4-Cl₂ CN 2509 2-F 3,5-Cl₂ CN 2510 2-F 2-F, 3-Cl CN 2511 2-F 2-F, 4-Cl CN 2512 2-F 2-F, 5-Cl CN 2513 2-F 2-F, 6-Cl CN 2514 2-F 2,6-F₂, 4-Cl CN 2515 2-F 3-F, 4-Cl CN 2516 2-F 3-Cl, 5-F CN 2517 2-F 2-Cl, 5-F CN 2518 2-F 3-CN, 4-Cl CN 2519 2-F 3-NO₂, 4-Cl CN 2520 2-F 2-F, 4-Br CN 2521 4-F 4-F CN 2522 4-F 4-Cl CN 2523 4-F 4-Br CN 2524 4-F H CN 2525 4-F 4-Me CN 2526 4-F 4-CN CN 2527 4-F 4-NO₂ CN 2528 4-F 4-OMe CN 2529 4-F 3-F CN 2530 4-F 3-Cl CN 2531 4-F 3-Br CN 2532 4-F 3-Me CN 2533 4-F 3-CN CN 2534 4-F 3-NO₂ CN 2535 4-F 3-OMe CN 2536 4-F 2-F CN 2537 4-F 2-Cl CN 2538 4-F 2-Br CN 2539 4-F 2-Me CN 2540 4-F 2-CN CN 2541 4-F 2-NO₂ CN 2542 4-F 2-OMe CN 2543 4-F 2,3-F₂ CN 2544 4-F 2,4-F₂ CN 2545 4-F 2,5-F₂ CN 2546 4-F 2,6-F₂ CN 2547 4-F 3,4-F₂ CN 2548 4-F 3,5-F₂ CN 2549 4-F 2,3-Cl₂ CN 2550 4-F 2,4-Cl₂ CN 2551 4-F 2,5-Cl₂ CN 2552 4-F 2,6-Cl₂ CN 2553 4-F 3,4-Cl₂ CN 2554 4-F 3,5-Cl₂ CN 2555 4-F 2-F, 3-Cl CN 2556 4-F 2-F, 4-Cl CN 2557 4-F 2-F, 5-Cl CN 2558 4-F 2-F, 6-Cl CN 2559 4-F 2,6-F₂, 4-Cl CN 2560 4-F 3-F, 4-Cl CN 2561 4-F 3-Cl, 5-F CN 2562 4-F 2-Cl, 5-F CN 2563 4-F 3-CN, 4-Cl CN 2564 4-F 3-NO₂, 4-Cl CN 2565 4-F 2-F, 4-Br CN 2566 2-Cl 4-F CN 2567 2-Cl 4-Cl CN 2568 2-Cl 4-Br CN 2569 2-Cl H CN 2570 2-Cl 4-Me CN 2571 2-Cl 4-CN CN 2572 2-Cl 4-NO₂ CN 2573 2-Cl 4-OMe CN 2574 2-Cl 3-F CN 2575 2-Cl 3-Cl CN 2576 2-Cl 3-Br CN 2577 2-Cl 3-Me CN 2578 2-Cl 3-CN CN 2579 2-Cl 3-NO₂ CN 2580 2-Cl 3-OMe CN 2581 2-Cl 2-F CN 2582 2-Cl 2-Cl CN 2583 2-Cl 2-Br CN 2584 2-Cl 2-Me CN 2585 2-Cl 2-CN CN 2586 2-Cl 2-NO₂ CN 2587 2-Cl 2-OMe CN 2588 2-Cl 2,3-F₂ CN 2589 2-Cl 2,4-F₂ CN 2590 2-Cl 2,5-F₂ CN 2591 2-Cl 2,6-F₂ CN 2592 2-Cl 3,4-F₂ CN 2593 2-Cl 3,5-F₂ CN 2594 2-Cl 2,3-Cl₂ CN 2595 2-Cl 2,4-Cl₂ CN 2596 2-Cl 2,5-Cl₂ CN 2597 2-Cl 2,6-Cl₂ CN 2598 2-Cl 3,4-Cl₂ CN 2599 2-Cl 3,5-Cl₂ CN 2600 2-Cl 2-F, 3-Cl CN 2601 2-Cl 2-F, 4-Cl CN 2602 2-Cl 2-F, 5-Cl CN 2603 2-Cl 2-F, 6-Cl CN 2604 2-Cl 2,6-F₂, 4-Cl CN 2605 2-Cl 3-F, 4-Cl CN 2606 2-Cl 3-Cl, 5-F CN 2607 2-Cl 2-Cl, 5-F CN 2608 2-Cl 3-CN, 4-Cl CN 2609 2-Cl 3-NO₂, 4-Cl CN 2610 2-Cl 2-F, 4-Br CN 2611 4-Cl 4-F CN 2612 4-Cl 4-Cl CN 2613 4-Cl 4-Br CN 2614 4-Cl H CN 2615 4-Cl 4-Me CN 2616 4-Cl 4-CN CN 2617 4-Cl 4-NO₂ CN 2618 4-Cl 4-OMe CN 2619 4-Cl 3-F CN 2620 4-Cl 3-Cl CN 2621 4-Cl 3-Br CN 2622 4-Cl 3-Me CN 2623 4-Cl 3-CN CN 2624 4-Cl 3-NO₂ CN 2625 4-Cl 3-OMe CN 2626 4-Cl 2-F CN 2627 4-Cl 2-Cl CN 2628 4-Cl 2-Br CN 2629 4-Cl 2-Me CN 2630 4-Cl 2-CN CN 2631 4-Cl 2-NO₂ CN 2632 4-Cl 2-OMe CN 2633 4-Cl 2,3-F₂ CN 2634 4-Cl 2,4-F₂ CN 2635 4-Cl 2,5-F₂ CN 2636 4-Cl 2,6-F₂ CN 2637 4-Cl 3,4-F₂ CN 2638 4-Cl 3,5-F₂ CN 2639 4-Cl 2,3-Cl₂ CN 2640 4-Cl 2,4-Cl₂ CN 2641 4-Cl 2,5-Cl₂ CN 2642 4-Cl 2,6-Cl₂ CN 2643 4-Cl 3,4-Cl₂ CN 2644 4-Cl 3,5-Cl₂ CN 2645 4-Cl 2-F, 3-Cl CN 2646 4-Cl 2-F, 4-Cl CN 2647 4-Cl 2-F, 5-Cl CN 2648 4-Cl 2-F, 6-Cl CN 2649 4-Cl 2,6-F₂, 4-Cl CN 2650 4-Cl 3-F, 4-Cl CN 2651 4-Cl 3-Cl, 5-F CN 2652 4-Cl 2-Cl, 5-F CN 2653 4-Cl 3-CN, 4-Cl CN 2654 4-Cl 3-NO₂, 4-Cl CN 2655 4-Cl 2-F, 4-Br CN 2656 6-OCF₂H 4-F CN 2657 6-OCF₂H 4-Cl CN 2658 6-OCF₂H 4-Br CN 2659 6-OCF₂H H CN 2660 6-OCF₂H 4-Me CN 2661 6-OCF₂H 4-CN CN 2662 6-OCF₂H 4-NO₂ CN 2663 6-OCF₂H 4-OMe CN 2664 6-OCF₂H 3-F CN 2665 6-OCF₂H 3-Cl CN 2666 6-OCF₂H 3-Br CN 2667 6-OCF₂H 3-Me CN 2668 6-OCF₂H 3-CN CN 2669 6-OCF₂H 3-NO₂ CN 2670 6-OCF₂H 3-OMe CN 2671 6-OCF₂H 2-F CN 2672 6-OCF₂H 2-Cl CN 2673 6-OCF₂H 2-Br CN 2674 6-OCF₂H 2-Me CN 2675 6-OCF₂H 2-CN CN 2676 6-OCF₂H 2-NO₂ CN 2677 6-OCF₂H 2-OMe CN 2678 6-OCF₂H 2,3-F₂ CN 2679 6-OCF₂H 2,4-F₂ CN 2680 6-OCF₂H 2,5-F₂ CN 2681 6-OCF₂H 2,6-F₂ CN 2682 6-OCF₂H 3,4-F₂ CN 2683 6-OCF₂H 3,5-F₂ CN 2684 6-OCF₂H 2,3-Cl₂ CN 2685 6-OCF₂H 2,4-Cl₂ CN 2686 6-OCF₂H 2,5-Cl₂ CN 2687 6-OCF₂H 2,6-Cl₂ CN 2688 6-OCF₂H 3,4-Cl₂ CN 2689 6-OCF₂H 3,5-Cl₂ CN 2690 6-OCF₂H 2-F, 3-Cl CN 2691 6-OCF₂H 2-F, 4-Cl CN 2692 6-OCF₂H 2-F, 5-Cl CN 2693 6-OCF₂H 2-F, 6-Cl CN 2694 6-OCF₂H 2,6-F₂, 4-Cl CN 2695 6-OCF₂H 3-F, 4-Cl CN 2696 6-OCF₂H 3-Cl, 5-F CN 2697 6-OCF₂H 2-Cl, 5-F CN 2698 6-OCF₂H 3-CN, 4-Cl CN 2699 6-OCF₂H 3-NO₂, 4-Cl CN 2700 6-OCF₂H 2-F, 4-Br CN 2701 H 4-F NO₂ 2702 H 4-Cl NO₂ 2703 H 4-Br NO₂ 2704 H H NO₂ 2705 H 4-Me NO₂ 2706 H 4-CN NO₂ 2707 H 4-NO₂ NO₂ 2708 H 4-OMe NO₂ 2709 H 3-F NO₂ 2710 H 3-Cl NO₂ 2711 H 3-Br NO₂ 2712 H 3-Me NO₂ 2713 H 3-CN NO₂ 2714 H 3-NO₂ NO₂ 2715 H 3-OMe NO₂ 2716 H 2-F NO₂ 2717 H 2-Cl NO₂ 2718 H 2-Br NO₂ 2719 H 2-Me NO₂ 2720 H 2-CN NO₂ 2721 H 2-NO₂ NO₂ 2722 H 2-OMe NO₂ 2723 H 2,3-F₂ NO₂ 2724 H 2,4-F₂ NO₂ 2725 H 2,5-F₂ NO₂ 2726 H 2,6-F₂ NO₂ 2727 H 3,4-F₂ NO₂ 2728 H 3,5-F₂ NO₂ 2729 H 2,3-Cl₂ NO₂ 2730 H 2,4-Cl₂ NO₂ 2731 H 2,5-Cl₂ NO₂ 2732 H 2,6-Cl₂ NO₂ 2733 H 3,4-Cl₂ NO₂ 2734 H 3,5-Cl₂ NO₂ 2735 H 2-F, 3-Cl NO₂ 2736 H 2-F, 4-Cl NO₂ 2737 H 2-F, 5-Cl NO₂ 2738 H 2-F, 6-Cl NO₂ 2739 H 2,6-F₂, 4-Cl NO₂ 2740 H 3-F, 4-Cl NO₂ 2741 H 3-Cl, 5-F NO₂ 2742 H 2-Cl, 5-F NO₂ 2743 H 3-CN, 4-Cl NO₂ 2744 H 3-NO₂, 4-Cl NO₂ 2745 H 2-F, 4-Br NO₂ 2746 6-F 4-F NO₂ 2747 6-F 4-Cl NO₂ 2748 6-F 4-Br NO₂ 2749 6-F H NO₂ 2750 6-F 4-Me NO₂ 2751 6-F 4-CN NO₂ 2752 6-F 4-NO₂ NO₂ 2753 6-F 4-OMe NO₂ 2754 6-F 3-F NO₂ 2755 6-F 3-Cl NO₂ 2756 6-F 3-Br NO₂ 2757 6-F 3-Me NO₂ 2758 6-F 3-CN NO₂ 2759 6-F 3-NO₂ NO₂ 2760 6-F 3-OMe NO₂ 2761 6-F 2-F NO₂ 2762 6-F 2-Cl NO₂ 2763 6-F 2-Br NO₂ 2764 6-F 2-Me NO₂ 2765 6-F 2-CN NO₂ 2766 6-F 2-NO₂ NO₂ 2767 6-F 2-OMe NO₂ 2768 6-F 2,3-F₂ NO₂ 2769 6-F 2,4-F₂ NO₂ 2770 6-F 2,5-F₂ NO₂ 2771 6-F 2,6-F₂ NO₂ 2772 6-F 3,4-F₂ NO₂ 2773 6-F 3,5-F₂ NO₂ 2774 6-F 2,3-Cl₂ NO₂ 2775 6-F 2,4-Cl₂ NO₂ 2776 6-F 2,5-Cl₂ NO₂ 2777 6-F 2,6-Cl₂ NO₂ 2778 6-F 3,4-Cl₂ NO₂ 2779 6-F 3,5-Cl₂ NO₂ 2780 6-F 2-F, 3-Cl NO₂ 2781 6-F 2-F, 4-Cl NO₂ 2782 6-F 2-F, 5-Cl NO₂ 2783 6-F 2-F, 6-Cl NO₂ 2784 6-F 2,6-F₂, 4-Cl NO₂ 2785 6-F 3-F, 4-Cl NO₂ 2786 6-F 3-Cl, 5-F NO₂ 2787 6-F 2-Cl, 5-F NO₂ 2788 6-F 3-CN, 4-Cl NO₂ 2789 6-F 3-NO₂, 4-Cl NO₂ 2790 6-F 2-F, 4-Br NO₂ 2791 6-Cl 4-F NO₂ 2792 6-Cl 4-Cl NO₂ 2793 6-Cl 4-Br NO₂ 2794 6-Cl H NO₂ 2795 6-Cl 4-Me NO₂ 2796 6-Cl 4-CN NO₂ 2797 6-Cl 4-NO₂ NO₂ 2798 6-Cl 4-OMe NO₂ 2799 6-Cl 3-F NO₂ 2800 6-Cl 3-Cl NO₂ 2801 6-Cl 3-Br NO₂ 2802 6-Cl 3-Me NO₂ 2803 6-Cl 3-CN NO₂ 2804 6-Cl 3-NO₂ NO₂ 2805 6-Cl 3-OMe NO₂ 2806 6-Cl 2-F NO₂ 2807 6-Cl 2-Cl NO₂ 2808 6-Cl 2-Br NO₂ 2809 6-Cl 2-Me NO₂ 2810 6-Cl 2-CN NO₂ 2811 6-Cl 2-NO₂ NO₂ 2812 6-Cl 2-OMe NO₂ 2813 6-Cl 2,3-F₂ NO₂ 2814 6-Cl 2,4-F₂ NO₂ 2815 6-Cl 2,5-F₂ NO₂ 2816 6-Cl 2,6-F₂ NO₂ 2817 6-Cl 3,4-F₂ NO₂ 2818 6-Cl 3,5-F₂ NO₂ 2819 6-Cl 2,3-Cl₂ NO₂ 2820 6-Cl 2,4-Cl₂ NO₂ 2821 6-Cl 2,5-Cl₂ NO₂ 2822 6-Cl 2,6-Cl₂ NO₂ 2823 6-Cl 3,4-Cl₂ NO₂ 2824 6-Cl 3,5-Cl₂ NO₂ 2825 6-Cl 2-F, 3-Cl NO₂ 2826 6-Cl 2-F, 4-Cl NO₂ 2827 6-Cl 2-F, 5-Cl NO₂ 2828 6-Cl 2-F, 6-Cl NO₂ 2829 6-Cl 2,6-F₂, 4-Cl NO₂ 2830 6-Cl 3-F, 4-Cl NO₂ 2831 6-Cl 3-Cl, 5-F NO₂ 2832 6-Cl 2-Cl, 5-F NO₂ 2833 6-Cl 3-CN, 4-Cl NO₂ 2834 6-Cl 3-NO₂, 4-Cl NO₂ 2835 6-Cl 2-F, 4-Br NO₂ 2836 6-Br 4-F NO₂ 2837 6-Br 4-Cl NO₂ 2838 6-Br 4-Br NO₂ 2839 6-Br H NO₂ 2840 6-Br 4-Me NO₂ 2841 6-Br 4-CN NO₂ 2842 6-Br 4-NO₂ NO₂ 2843 6-Br 4-OMe NO₂ 2844 6-Br 3-F NO₂ 2845 6-Br 3-Cl NO₂ 2846 6-Br 3-Br NO₂ 2847 6-Br 3-Me NO₂ 2848 6-Br 3-CN NO₂ 2849 6-Br 3-NO₂ NO₂ 2850 6-Br 3-OMe NO₂ 2851 6-Br 2-F NO₂ 2852 6-Br 2-Cl NO₂ 2853 6-Br 2-Br NO₂ 2854 6-Br 2-Me NO₂ 2855 6-Br 2-CN NO₂ 2856 6-Br 2-NO₂ NO₂ 2857 6-Br 2-OMe NO₂ 2858 6-Br 2,3-F₂ NO₂ 2859 6-Br 2,4-F₂ NO₂ 2860 6-Br 2,5-F₂ NO₂ 2861 6-Br 2,6-F₂ NO₂ 2862 6-Br 3,4-F₂ NO₂ 2863 6-Br 3,5-F₂ NO₂ 2864 6-Br 2,3-Cl₂ NO₂ 2865 6-Br 2,4-Cl₂ NO₂ 2866 6-Br 2,5-Cl₂ NO₂ 2867 6-Br 2,6-Cl₂ NO₂ 2868 6-Br 3,4-Cl₂ NO₂ 2869 6-Br 3,5-Cl₂ NO₂ 2870 6-Br 2-F, 3-Cl NO₂ 2871 6-Br 2-F, 4-Cl NO₂ 2872 6-Br 2-F, 5-Cl NO₂ 2873 6-Br 2-F, 6-Cl NO₂ 2874 6-Br 2,6-F₂, 4-Cl NO₂ 2875 6-Br 3-F, 4-Cl NO₂ 2876 6-Br 3-Cl, 5-F NO₂ 2877 6-Br 2-Cl, 5-F NO₂ 2878 6-Br 3-CN, 4-Cl NO₂ 2879 6-Br 3-NO₂, 4-Cl NO₂ 2880 6-Br 2-F, 4-Br NO₂ 2881 6-CN 4-F NO₂ 2882 6-CN 4-Cl NO₂ 2883 6-CN 4-Br NO₂ 2884 6-CN H NO₂ 2885 6-CN 4-Me NO₂ 2886 6-CN 4-CN NO₂ 2887 6-CN 4-NO₂ NO₂ 2888 6-CN 4-OMe NO₂ 2889 6-CN 3-F NO₂ 2890 6-CN 3-Cl NO₂ 2891 6-CN 3-Br NO₂ 2892 6-CN 3-Me NO₂ 2893 6-CN 3-CN NO₂ 2894 6-CN 3-NO₂ NO₂ 2895 6-CN 3-OMe NO₂ 2896 6-CN 2-F NO₂ 2897 6-CN 2-Cl NO₂ 2898 6-CN 2-Br NO₂ 2899 6-CN 2-Me NO₂ 2900 6-CN 2-CN NO₂ 2901 6-CN 2-NO₂ NO₂ 2902 6-CN 2-OMe NO₂ 2903 6-CN 2,3-F₂ NO₂ 2904 6-CN 2,4-F₂ NO₂ 2905 6-CN 2,5-F₂ NO₂ 2906 6-CN 2,6-F₂ NO₂ 2907 6-CN 3,4-F₂ NO₂ 2908 6-CN 3,5-F₂ NO₂ 2909 6-CN 2,3-Cl₂ NO₂ 2910 6-CN 2,4-Cl₂ NO₂ 2911 6-CN 2,5-Cl₂ NO₂ 2912 6-CN 2,6-Cl₂ NO₂ 2913 6-CN 3,4-Cl₂ NO₂ 2914 6-CN 3,5-Cl₂ NO₂ 2915 6-CN 2-F, 3-Cl NO₂ 2916 6-CN 2-F, 4-Cl NO₂ 2917 6-CN 2-F, 5-Cl NO₂ 2918 6-CN 2-F, 6-Cl NO₂ 2919 6-CN 2,6-F₂, 4-Cl NO₂ 2920 6-CN 3-F, 4-Cl NO₂ 2921 6-CN 3-Cl, 5-F NO₂ 2922 6-CN 2-Cl, 5-F NO₂ 2923 6-CN 3-CN, 4-Cl NO₂ 2924 6-CN 3-NO₂, 4-Cl NO₂ 2925 6-CN 2-F, 4-Br NO₂ 2926 6-Me 4-F NO₂ 2927 6-Me 4-Cl NO₂ 2928 6-Me 4-Br NO₂ 2929 6-Me H NO₂ 2930 6-Me 4-Me NO₂ 2931 6-Me 4-CN NO₂ 2932 6-Me 4-NO₂ NO₂ 2933 6-Me 4-OMe NO₂ 2934 6-Me 3-F NO₂ 2935 6-Me 3-Cl NO₂ 2936 6-Me 3-Br NO₂ 2937 6-Me 3-Me NO₂ 2938 6-Me 3-CN NO₂ 2939 6-Me 3-NO₂ NO₂ 2940 6-Me 3-OMe NO₂ 2941 6-Me 2-F NO₂ 2942 6-Me 2-Cl NO₂ 2943 6-Me 2-Br NO₂ 2944 6-Me 2-Me NO₂ 2945 6-Me 2-CN NO₂ 2946 6-Me 2-NO₂ NO₂ 2947 6-Me 2-OMe NO₂ 2948 6-Me 2,3-F₂ NO₂ 2949 6-Me 2,4-F₂ NO₂ 2950 6-Me 2,5-F₂ NO₂ 2951 6-Me 2,6-F₂ NO₂ 2952 6-Me 3,4-F₂ NO₂ 2953 6-Me 3,5-F₂ NO₂ 2954 6-Me 2,3-Cl₂ NO₂ 2955 6-Me 2,4-Cl₂ NO₂ 2956 6-Me 2,5-Cl₂ NO₂ 2957 6-Me 2,6-Cl₂ NO₂ 2958 6-Me 3,4-Cl₂ NO₂ 2959 6-Me 3,5-Cl₂ NO₂ 2960 6-Me 2-F, 3-Cl NO₂ 2961 6-Me 2-F, 4-Cl NO₂ 2962 6-Me 2-F, 5-Cl NO₂ 2963 6-Me 2-F, 6-Cl NO₂ 2964 6-Me 2,6-F₂, 4-Cl NO₂ 2965 6-Me 3-F, 4-Cl NO₂ 2966 6-Me 3-Cl, 5-F NO₂ 2967 6-Me 2-Cl, 5-F NO₂ 2968 6-Me 3-CN, 4-Cl NO₂ 2969 6-Me 3-NO₂, 4-Cl NO₂ 2970 6-Me 2-F, 4-Br NO₂ 2971 6-OMe 4-F NO₂ 2972 6-OMe 4-Cl NO₂ 2973 6-OMe 4-Br NO₂ 2974 6-OMe H NO₂ 2975 6-OMe 4-Me NO₂ 2976 6-OMe 4-CN NO₂ 2977 6-OMe 4-NO₂ NO₂ 2978 6-OMe 4-OMe NO₂ 2979 6-OMe 3-F NO₂ 2980 6-OMe 3-Cl NO₂ 2981 6-OMe 3-Br NO₂ 2982 6-OMe 3-Me NO₂ 2983 6-OMe 3-CN NO₂ 2984 6-OMe 3-NO₂ NO₂ 2985 6-OMe 3-OMe NO₂ 2986 6-OMe 2-F NO₂ 2987 6-OMe 2-Cl NO₂ 2988 6-OMe 2-Br NO₂ 2989 6-OMe 2-Me NO₂ 2990 6-OMe 2-CN NO₂ 2991 6-OMe 2-NO₂ NO₂ 2992 6-OMe 2-OMe NO₂ 2993 6-OMe 2,3-F₂ NO₂ 2994 6-OMe 2,4-F₂ NO₂ 2995 6-OMe 2,5-F₂ NO₂ 2996 6-OMe 2,6-F₂ NO₂ 2997 6-OMe 3,4-F₂ NO₂ 2998 6-OMe 3,5-F₂ NO₂ 2999 6-OMe 2,3-Cl₂ NO₂ 3000 6-OMe 2,4-Cl₂ NO₂ 3001 6-OMe 2,5-Cl₂ NO₂ 3002 6-OMe 2,6-Cl₂ NO₂ 3003 6-OMe 3,4-Cl₂ NO₂ 3004 6-OMe 3,5-Cl₂ NO₂ 3005 6-OMe 2-F, 3-Cl NO₂ 3006 6-OMe 2-F, 4-Cl NO₂ 3007 6-OMe 2-F, 5-Cl NO₂ 3008 6-OMe 2-F, 6-Cl NO₂ 3009 6-OMe 2,6-F₂, 4-Cl NO₂ 3010 6-OMe 3-F, 4-Cl NO₂ 3011 6-OMe 3-Cl, 5-F NO₂ 3012 6-OMe 2-Cl, 5-F NO₂ 3013 6-OMe 3-CN, 4-Cl NO₂ 3014 6-OMe 3-NO₂, 4-Cl NO₂ 3015 6-OMe 2-F, 4-Br NO₂ 3016 2-F 4-F NO₂ 3017 2-F 4-Cl NO₂ 3018 2-F 4-Br NO₂ 3019 2-F H NO₂ 3020 2-F 4-Me NO₂ 3021 2-F 4-CN NO₂ 3022 2-F 4-NO₂ NO₂ 3023 2-F 4-OMe NO₂ 3024 2-F 3-F NO₂ 3025 2-F 3-Cl NO₂ 3026 2-F 3-Br NO₂ 3027 2-F 3-Me NO₂ 3028 2-F 3-CN NO₂ 3029 2-F 3-NO₂ NO₂ 3030 2-F 3-OMe NO₂ 3031 2-F 2-F NO₂ 3032 2-F 2-Cl NO₂ 3033 2-F 2-Br NO₂ 3034 2-F 2-Me NO₂ 3035 2-F 2-CN NO₂ 3036 2-F 2-NO₂ NO₂ 3037 2-F 2-OMe NO₂ 3038 2-F 2,3-F₂ NO₂ 3039 2-F 2,4-F₂ NO₂ 3040 2-F 2,5-F₂ NO₂ 3041 2-F 2,6-F₂ NO₂ 3042 2-F 3,4-F₂ NO₂ 3043 2-F 3,5-F₂ NO₂ 3044 2-F 2,3-Cl₂ NO₂ 3045 2-F 2,4-Cl₂ NO₂ 3046 2-F 2,5-Cl₂ NO₂ 3047 2-F 2,6-Cl₂ NO₂ 3048 2-F 3,4-Cl₂ NO₂ 3049 2-F 3,5-Cl₂ NO₂ 3050 2-F 2-F, 3-Cl NO₂ 3051 2-F 2-F, 4-Cl NO₂ 3052 2-F 2-F, 5-Cl NO₂ 3053 2-F 2-F, 6-Cl NO₂ 3054 2-F 2,6-F₂, 4-Cl NO₂ 3055 2-F 3-F, 4-Cl NO₂ 3056 2-F 3-Cl, 5-F NO₂ 3057 2-F 2-Cl, 5-F NO₂ 3058 2-F 3-CN, 4-Cl NO₂ 3059 2-F 3-NO₂, 4-Cl NO₂ 3060 2-F 2-F, 4-Br NO₂ 3061 4-F 4-F NO₂ 3062 4-F 4-Cl NO₂ 3063 4-F 4-Br NO₂ 3064 4-F H NO₂ 3065 4-F 4-Me NO₂ 3066 4-F 4-CN NO₂ 3067 4-F 4-NO₂ NO₂ 3068 4-F 4-OMe NO₂ 3069 4-F 3-F NO₂ 3070 4-F 3-Cl NO₂ 3071 4-F 3-Br NO₂ 3072 4-F 3-Me NO₂ 3073 4-F 3-CN NO₂ 3074 4-F 3-NO₂ NO₂ 3075 4-F 3-OMe NO₂ 3076 4-F 2-F NO₂ 3077 4-F 2-Cl NO₂ 3078 4-F 2-Br NO₂ 3079 4-F 2-Me NO₂ 3080 4-F 2-CN NO₂ 3081 4-F 2-NO₂ NO₂ 3082 4-F 2-OMe NO₂ 3083 4-F 2,3-F₂ NO₂ 3084 4-F 2,4-F₂ NO₂ 3085 4-F 2,5-F₂ NO₂ 3086 4-F 2,6-F₂ NO₂ 3087 4-F 3,4-F₂ NO₂ 3088 4-F 3,5-F₂ NO₂ 3089 4-F 2,3-Cl₂ NO₂ 3090 4-F 2,4-Cl₂ NO₂ 3091 4-F 2,5-Cl₂ NO₂ 3092 4-F 2,6-Cl₂ NO₂ 3093 4-F 3,4-Cl₂ NO₂ 3094 4-F 3,5-Cl₂ NO₂ 3095 4-F 2-F, 3-Cl NO₂ 3096 4-F 2-F, 4-Cl NO₂ 3097 4-F 2-F, 5-Cl NO₂ 3098 4-F 2-F, 6-Cl NO₂ 3099 4-F 2,6-F₂, 4-Cl NO₂ 3100 4-F 3-F, 4-Cl NO₂ 3101 4-F 3-Cl, 5-F NO₂ 3102 4-F 2-Cl, 5-F NO₂ 3103 4-F 3-CN, 4-Cl NO₂ 3104 4-F 3-NO₂, 4-Cl NO₂ 3105 4-F 2-F, 4-Br NO₂ 3106 2-Cl 4-F NO₂ 3107 2-Cl 4-Cl NO₂ 3108 2-Cl 4-Br NO₂ 3109 2-Cl H NO₂ 3110 2-Cl 4-Me NO₂ 3111 2-Cl 4-CN NO₂ 3112 2-Cl 4-NO₂ NO₂ 3113 2-Cl 4-OMe NO₂ 3114 2-Cl 3-F NO₂ 3115 2-Cl 3-Cl NO₂ 3116 2-Cl 3-Br NO₂ 3117 2-Cl 3-Me NO₂ 3118 2-Cl 3-CN NO₂ 3119 2-Cl 3-NO₂ NO₂ 3120 2-Cl 3-OMe NO₂ 3121 2-Cl 2-F NO₂ 3122 2-Cl 2-Cl NO₂ 3123 2-Cl 2-Br NO₂ 3124 2-Cl 2-Me NO₂ 3125 2-Cl 2-CN NO₂ 3126 2-Cl 2-NO₂ NO₂ 3127 2-Cl 2-OMe NO₂ 3128 2-Cl 2,3-F₂ NO₂ 3129 2-Cl 2,4-F₂ NO₂ 3130 2-Cl 2,5-F₂ NO₂ 3131 2-Cl 2,6-F₂ NO₂ 3132 2-Cl 3,4-F₂ NO₂ 3133 2-Cl 3,5-F₂ NO₂ 3134 2-Cl 2,3-Cl₂ NO₂ 3135 2-Cl 2,4-Cl₂ NO₂ 3136 2-Cl 2,5-Cl₂ NO₂ 3137 2-Cl 2,6-Cl₂ NO₂ 3138 2-Cl 3,4-Cl₂ NO₂ 3139 2-Cl 3,5-Cl₂ NO₂ 3140 2-Cl 2-F, 3-Cl NO₂ 3141 2-Cl 2-F, 4-Cl NO₂ 3142 2-Cl 2-F, 5-Cl NO₂ 3143 2-Cl 2-F, 6-Cl NO₂ 3144 2-Cl 2,6-F₂, 4-Cl NO₂ 3145 2-Cl 3-F, 4-Cl NO₂ 3146 2-Cl 3-Cl, 5-F NO₂ 3147 2-Cl 2-Cl, 5-F NO₂ 3148 2-Cl 3-CN, 4-Cl NO₂ 3149 2-Cl 3-NO₂, 4-Cl NO₂ 3150 2-Cl 2-F, 4-Br NO₂ 3151 4-Cl 4-F NO₂ 3152 4-Cl 4-Cl NO₂ 3153 4-Cl 4-Br NO₂ 3154 4-Cl H NO₂ 3155 4-Cl 4-Me NO₂ 3156 4-Cl 4-CN NO₂ 3157 4-Cl 4-NO₂ NO₂ 3158 4-Cl 4-OMe NO₂ 3159 4-Cl 3-F NO₂ 3160 4-Cl 3-Cl NO₂ 3161 4-Cl 3-Br NO₂ 3162 4-Cl 3-Me NO₂ 3163 4-Cl 3-CN NO₂ 3164 4-Cl 3-NO₂ NO₂ 3165 4-Cl 3-OMe NO₂ 3166 4-Cl 2-F NO₂ 3167 4-Cl 2-Cl NO₂ 3168 4-Cl 2-Br NO₂ 3169 4-Cl 2-Me NO₂ 3170 4-Cl 2-CN NO₂ 3171 4-Cl 2-NO₂ NO₂ 3172 4-Cl 2-OMe NO₂ 3173 4-Cl 2,3-F₂ NO₂ 3174 4-Cl 2,4-F₂ NO₂ 3175 4-Cl 2,5-F₂ NO₂ 3176 4-Cl 2,6-F₂ NO₂ 3177 4-Cl 3,4-F₂ NO₂ 3178 4-Cl 3,5-F₂ NO₂ 3179 4-Cl 2,3-Cl₂ NO₂ 3180 4-Cl 2,4-Cl₂ NO₂ 3181 4-Cl 2,5-Cl₂ NO₂ 3182 4-Cl 2,6-Cl₂ NO₂ 3183 4-Cl 3,4-Cl₂ NO₂ 3184 4-Cl 3,5-Cl₂ NO₂ 3185 4-Cl 2-F, 3-Cl NO₂ 3186 4-Cl 2-F, 4-Cl NO₂ 3187 4-Cl 2-F, 5-Cl NO₂ 3188 4-Cl 2-F, 6-Cl NO₂ 3189 4-Cl 2,6-F₂, 4-Cl NO₂ 3190 4-Cl 3-F, 4-Cl NO₂ 3191 4-Cl 3-Cl, 5-F NO₂ 3192 4-Cl 2-Cl, 5-F NO₂ 3193 4-Cl 3-CN, 4-Cl NO₂ 3194 4-Cl 3-NO₂, 4-Cl NO₂ 3195 4-Cl 2-F, 4-Br NO₂ 3196 6-OCF₂H 4-F NO₂ 3197 6-OCF₂H 4-Cl NO₂ 3198 6-OCF₂H 4-Br NO₂ 3199 6-OCF₂H H NO₂ 3200 6-OCF₂H 4-Me NO₂ 3201 6-OCF₂H 4-CN NO₂ 3202 6-OCF₂H 4-NO₂ NO₂ 3203 6-OCF₂H 4-OMe NO₂ 3204 6-OCF₂H 3-F NO₂ 3205 6-OCF₂H 3-Cl NO₂ 3206 6-OCF₂H 3-Br NO₂ 3207 6-OCF₂H 3-Me NO₂ 3208 6-OCF₂H 3-CN NO₂ 3209 6-OCF₂H 3-NO₂ NO₂ 3210 6-OCF₂H 3-OMe NO₂ 3211 6-OCF₂H 2-F NO₂ 3212 6-OCF₂H 2-Cl NO₂ 3213 6-OCF₂H 2-Br NO₂ 3214 6-OCF₂H 2-Me NO₂ 3215 6-OCF₂H 2-CN NO₂ 3216 6-OCF₂H 2-NO₂ NO₂ 3217 6-OCF₂H 2-OMe NO₂ 3218 6-OCF₂H 2,3-F₂ NO₂ 3219 6-OCF₂H 2,4-F₂ NO₂ 3220 6-OCF₂H 2,5-F₂ NO₂ 3221 6-OCF₂H 2,6-F₂ NO₂ 3222 6-OCF₂H 3,4-F₂ NO₂ 3223 6-OCF₂H 3,5-F₂ NO₂ 3224 6-OCF₂H 2,3-Cl₂ NO₂ 3225 6-OCF₂H 2,4-Cl₂ NO₂ 3226 6-OCF₂H 2,5-Cl₂ NO₂ 3227 6-OCF₂H 2,6-Cl₂ NO₂ 3228 6-OCF₂H 3,4-Cl₂ NO₂ 3229 6-OCF₂H 3,5-Cl₂ NO₂ 3230 6-OCF₂H 2-F, 3-Cl NO₂ 3231 6-OCF₂H 2-F, 4-Cl NO₂ 3232 6-OCF₂H 2-F, 5-Cl NO₂ 3233 6-OCF₂H 2-F, 6-Cl NO₂ 3234 6-OCF₂H 2,6-F₂, 4-Cl NO₂ 3235 6-OCF₂H 3-F, 4-Cl NO₂ 3236 6-OCF₂H 3-Cl, 5-F NO₂ 3237 6-OCF₂H 2-Cl, 5-F NO₂ 3238 6-OCF₂H 3-CN, 4-Cl NO₂ 3239 6-OCF₂H 3-NO₂, 4-Cl NO₂ 3240 6-OCF₂H 2-F, 4-Br NO₂ 3241 H 4-F CO₂Me 3242 H 4-Cl CO₂Me 3243 H 4-Br CO₂Me 3244 H H CO₂Me 3245 H 4-Me CO₂Me 3246 H 4-CN CO₂Me 3247 H 4-NO₂ CO₂Me 3248 H 4-OMe CO₂Me 3249 H 3-F CO₂Me 3250 H 3-Cl CO₂Me 3251 H 3-Br CO₂Me 3252 H 3-Me CO₂Me 3253 H 3-CN CO₂Me 3254 H 3-NO₂ CO₂Me 3255 H 3-OMe CO₂Me 3256 H 2-F CO₂Me 3257 H 2-Cl CO₂Me 3258 H 2-Br CO₂Me 3259 H 2-Me CO₂Me 3260 H 2-CN CO₂Me 3261 H 2-NO₂ CO₂Me 3262 H 2-OMe CO₂Me 3263 H 2,3-F₂ CO₂Me 3264 H 2,4-F₂ CO₂Me 3265 H 2,5-F₂ CO₂Me 3266 H 2,6-F₂ CO₂Me 3267 H 3,4-F₂ CO₂Me 3268 H 3,5-F₂ CO₂Me 3269 H 2,3-Cl₂ CO₂Me 3270 H 2,4-Cl₂ CO₂Me 3271 H 2,5-Cl₂ CO₂Me 3272 H 2,6-Cl₂ CO₂Me 3273 H 3,4-Cl₂ CO₂Me 3274 H 3,5-Cl₂ CO₂Me 3275 H 2-F, 3-Cl CO₂Me 3276 H 2-F, 4-Cl CO₂Me 3277 H 2-F, 5-Cl CO₂Me 3278 H 2-F, 6-Cl CO₂Me 3279 H 2,6-F₂, 4-Cl CO₂Me 3280 H 3-F, 4-Cl CO₂Me 3281 H 3-Cl, 5-F CO₂Me 3282 H 2-Cl, 5-F CO₂Me 3283 H 3-CN, 4-Cl CO₂Me 3284 H 3-NO₂, 4-Cl CO₂Me 3285 H 2-F, 4-Br CO₂Me 3286 6-F 4-F CO₂Me 3287 6-F 4-Cl CO₂Me 3288 6-F 4-Br CO₂Me 3289 6-F H CO₂Me 3290 6-F 4-Me CO₂Me 3291 6-F 4-CN CO₂Me 3292 6-F 4-NO₂ CO₂Me 3293 6-F 4-OMe CO₂Me 3294 6-F 3-F CO₂Me 3295 6-F 3-Cl CO₂Me 3296 6-F 3-Br CO₂Me 3297 6-F 3-Me CO₂Me 3298 6-F 3-CN CO₂Me 3299 6-F 3-NO₂ CO₂Me 3300 6-F 3-OMe CO₂Me 3301 6-F 2-F CO₂Me 3302 6-F 2-Cl CO₂Me 3303 6-F 2-Br CO₂Me 3304 6-F 2-Me CO₂Me 3305 6-F 2-CN CO₂Me 3306 6-F 2-NO₂ CO₂Me 3307 6-F 2-OMe CO₂Me 3308 6-F 2,3-F₂ CO₂Me 3309 6-F 2,4-F₂ CO₂Me 3310 6-F 2,5-F₂ CO₂Me 3311 6-F 2,6-F₂ CO₂Me 3312 6-F 3,4-F₂ CO₂Me 3313 6-F 3,5-F₂ CO₂Me 3314 6-F 2,3-Cl₂ CO₂Me 3315 6-F 2,4-Cl₂ CO₂Me 3316 6-F 2,5-Cl₂ CO₂Me 3317 6-F 2,6-Cl₂ CO₂Me 3318 6-F 3,4-Cl₂ CO₂Me 3319 6-F 3,5-Cl₂ CO₂Me 3320 6-F 2-F, 3-Cl CO₂Me 3321 6-F 2-F, 4-Cl CO₂Me 3322 6-F 2-F, 5-Cl CO₂Me 3323 6-F 2-F, 6-Cl CO₂Me 3324 6-F 2,6-F₂, 4-Cl CO₂Me 3325 6-F 3-F, 4-Cl CO₂Me 3326 6-F 3-Cl, 5-F CO₂Me 3327 6-F 2-Cl, 5-F CO₂Me 3328 6-F 3-CN, 4-Cl CO₂Me 3329 6-F 3-NO₂, 4-Cl CO₂Me 3330 6-F 2-F, 4-Br CO₂Me 3331 6-Cl 4-F CO₂Me 3332 6-Cl 4-Cl CO₂Me 3333 6-Cl 4-Br CO₂Me 3334 6-Cl H CO₂Me 3335 6-Cl 4-Me CO₂Me 3336 6-Cl 4-CN CO₂Me 3337 6-Cl 4-NO₂ CO₂Me 3338 6-Cl 4-OMe CO₂Me 3339 6-Cl 3-F CO₂Me 3340 6-Cl 3-Cl CO₂Me 3341 6-Cl 3-Br CO₂Me 3342 6-Cl 3-Me CO₂Me 3343 6-Cl 3-CN CO₂Me 3344 6-Cl 3-NO₂ CO₂Me 3345 6-Cl 3-OMe CO₂Me 3346 6-Cl 2-F CO₂Me 3347 6-Cl 2-Cl CO₂Me 3348 6-Cl 2-Br CO₂Me 3349 6-Cl 2-Me CO₂Me 3350 6-Cl 2-CN CO₂Me 3351 6-Cl 2-NO₂ CO₂Me 3352 6-Cl 2-OMe CO₂Me 3353 6-Cl 2,3-F₂ CO₂Me 3354 6-Cl 2,4-F₂ CO₂Me 3355 6-Cl 2,5-F₂ CO₂Me 3356 6-Cl 2,6-F₂ CO₂Me 3357 6-Cl 3,4-F₂ CO₂Me 3358 6-Cl 3,5-F₂ CO₂Me 3359 6-Cl 2,3-Cl₂ CO₂Me 3360 6-Cl 2,4-Cl₂ CO₂Me 3361 6-Cl 2,5-Cl₂ CO₂Me 3362 6-Cl 2,6-Cl₂ CO₂Me 3363 6-Cl 3,4-Cl₂ CO₂Me 3364 6-Cl 3,5-Cl₂ CO₂Me 3365 6-Cl 2-F, 3-Cl CO₂Me 3366 6-Cl 2-F, 4-Cl CO₂Me 3367 6-Cl 2-F, 5-Cl CO₂Me 3368 6-Cl 2-F, 6-Cl CO₂Me 3369 6-Cl 2,6-F₂, 4-Cl CO₂Me 3370 6-Cl 3-F, 4-Cl CO₂Me 3371 6-Cl 3-Cl, 5-F CO₂Me 3372 6-Cl 2-Cl, 5-F CO₂Me 3373 6-Cl 3-CN, 4-Cl CO₂Me 3374 6-Cl 3-NO₂, 4-Cl CO₂Me 3375 6-Cl 2-F, 4-Br CO₂Me 3376 6-Br 4-F CO₂Me 3377 6-Br 4-Cl CO₂Me 3378 6-Br 4-Br CO₂Me 3379 6-Br H CO₂Me 3380 6-Br 4-Me CO₂Me 3381 6-Br 4-CN CO₂Me 3382 6-Br 4-NO₂ CO₂Me 3383 6-Br 4-OMe CO₂Me 3384 6-Br 3-F CO₂Me 3385 6-Br 3-Cl CO₂Me 3386 6-Br 3-Br CO₂Me 3387 6-Br 3-Me CO₂Me 3388 6-Br 3-CN CO₂Me 3389 6-Br 3-NO₂ CO₂Me 3390 6-Br 3-OMe CO₂Me 3391 6-Br 2-F CO₂Me 3392 6-Br 2-Cl CO₂Me 3393 6-Br 2-Br CO₂Me 3394 6-Br 2-Me CO₂Me 3395 6-Br 2-CN CO₂Me 3396 6-Br 2-NO₂ CO₂Me 3397 6-Br 2-OMe CO₂Me 3398 6-Br 2,3-F₂ CO₂Me 3399 6-Br 2,4-F₂ CO₂Me 3400 6-Br 2,5-F₂ CO₂Me 3401 6-Br 2,6-F₂ CO₂Me 3402 6-Br 3,4-F₂ CO₂Me 3403 6-Br 3,5-F₂ CO₂Me 3404 6-Br 2,3-Cl₂ CO₂Me 3405 6-Br 2,4-Cl₂ CO₂Me 3406 6-Br 2,5-Cl₂ CO₂Me 3407 6-Br 2,6-Cl₂ CO₂Me 3408 6-Br 3,4-Cl₂ CO₂Me 3409 6-Br 3,5-Cl₂ CO₂Me 3410 6-Br 2-F, 3-Cl CO₂Me 3411 6-Br 2-F, 4-Cl CO₂Me 3412 6-Br 2-F, 5-Cl CO₂Me 3413 6-Br 2-F, 6-Cl CO₂Me 3414 6-Br 2,6-F₂, 4-Cl CO₂Me 3415 6-Br 3-F, 4-Cl CO₂Me 3416 6-Br 3-Cl, 5-F CO₂Me 3417 6-Br 2-Cl, 5-F CO₂Me 3418 6-Br 3-CN, 4-Cl CO₂Me 3419 6-Br 3-NO₂, 4-Cl CO₂Me 3420 6-Br 2-F, 4-Br CO₂Me 3421 6-CN 4-F CO₂Me 3422 6-CN 4-Cl CO₂Me 3423 6-CN 4-Br CO₂Me 3424 6-CN H CO₂Me 3425 6-CN 4-Me CO₂Me 3426 6-CN 4-CN CO₂Me 3427 6-CN 4-NO₂ CO₂Me 3428 6-CN 4-OMe CO₂Me 3429 6-CN 3-F CO₂Me 3430 6-CN 3-Cl CO₂Me 3431 6-CN 3-Br CO₂Me 3432 6-CN 3-Me CO₂Me 3433 6-CN 3-CN CO₂Me 3434 6-CN 3-NO₂ CO₂Me 3435 6-CN 3-OMe CO₂Me 3436 6-CN 2-F CO₂Me 3437 6-CN 2-Cl CO₂Me 3438 6-CN 2-Br CO₂Me 3439 6-CN 2-Me CO₂Me 3440 6-CN 2-CN CO₂Me 3441 6-CN 2-NO₂ CO₂Me 3442 6-CN 2-OMe CO₂Me 3443 6-CN 2,3-F₂ CO₂Me 3444 6-CN 2,4-F₂ CO₂Me 3445 6-CN 2,5-F₂ CO₂Me 3446 6-CN 2,6-F₂ CO₂Me 3447 6-CN 3,4-F₂ CO₂Me 3448 6-CN 3,5-F₂ CO₂Me 3449 6-CN 2,3-Cl₂ CO₂Me 3450 6-CN 2,4-Cl₂ CO₂Me 3451 6-CN 2,5-Cl₂ CO₂Me 3452 6-CN 2,6-Cl₂ CO₂Me 3453 6-CN 3,4-Cl₂ CO₂Me 3454 6-CN 3,5-Cl₂ CO₂Me 3455 6-CN 2-F, 3-Cl CO₂Me 3456 6-CN 2-F, 4-Cl CO₂Me 3457 6-CN 2-F, 5-Cl CO₂Me 3458 6-CN 2-F, 6-Cl CO₂Me 3459 6-CN 2,6-F₂, 4-Cl CO₂Me 3460 6-CN 3-F, 4-Cl CO₂Me 3461 6-CN 3-Cl, 5-F CO₂Me 3462 6-CN 2-Cl, 5-F CO₂Me 3463 6-CN 3-CN, 4-Cl CO₂Me 3464 6-CN 3-NO₂, 4-Cl CO₂Me 3465 6-CN 2-F, 4-Br CO₂Me 3466 6-Me 4-F CO₂Me 3467 6-Me 4-Cl CO₂Me 3468 6-Me 4-Br CO₂Me 3469 6-Me H CO₂Me 3470 6-Me 4-Me CO₂Me 3471 6-Me 4-CN CO₂Me 3472 6-Me 4-NO₂ CO₂Me 3473 6-Me 4-OMe CO₂Me 3474 6-Me 3-F CO₂Me 3475 6-Me 3-Cl CO₂Me 3476 6-Me 3-Br CO₂Me 3477 6-Me 3-Me CO₂Me 3478 6-Me 3-CN CO₂Me 3479 6-Me 3-NO₂ CO₂Me 3480 6-Me 3-OMe CO₂Me 3481 6-Me 2-F CO₂Me 3482 6-Me 2-Cl CO₂Me 3483 6-Me 2-Br CO₂Me 3484 6-Me 2-Me CO₂Me 3485 6-Me 2-CN CO₂Me 3486 6-Me 2-NO₂ CO₂Me 3487 6-Me 2-OMe CO₂Me 3488 6-Me 2,3-F₂ CO₂Me 3489 6-Me 2,4-F₂ CO₂Me 3490 6-Me 2,5-F₂ CO₂Me 3491 6-Me 2,6-F₂ CO₂Me 3492 6-Me 3,4-F₂ CO₂Me 3493 6-Me 3,5-F₂ CO₂Me 3494 6-Me 2,3-Cl₂ CO₂Me 3495 6-Me 2,4-Cl₂ CO₂Me 3496 6-Me 2,5-Cl₂ CO₂Me 3497 6-Me 2,6-Cl₂ CO₂Me 3498 6-Me 3,4-Cl₂ CO₂Me 3499 6-Me 3,5-Cl₂ CO₂Me 3500 6-Me 2-F, 3-Cl CO₂Me 3501 6-Me 2-F, 4-Cl CO₂Me 3502 6-Me 2-F, 5-Cl CO₂Me 3503 6-Me 2-F, 6-Cl CO₂Me 3504 6-Me 2,6-F₂, 4-Cl CO₂Me 3505 6-Me 3-F, 4-Cl CO₂Me 3506 6-Me 3-Cl, 5-F CO₂Me 3507 6-Me 2-Cl, 5-F CO₂Me 3508 6-Me 3-CN, 4-Cl CO₂Me 3509 6-Me 3-NO₂, 4-Cl CO₂Me 3510 6-Me 2-F, 4-Br CO₂Me 3511 6-OMe 4-F CO₂Me 3512 6-OMe 4-Cl CO₂Me 3513 6-OMe 4-Br CO₂Me 3514 6-OMe H CO₂Me 3515 6-OMe 4-Me CO₂Me 3516 6-OMe 4-CN CO₂Me 3517 6-OMe 4-NO₂ CO₂Me 3518 6-OMe 4-OMe CO₂Me 3519 6-OMe 3-F CO₂Me 3520 6-OMe 3-Cl CO₂Me 3521 6-OMe 3-Br CO₂Me 3522 6-OMe 3-Me CO₂Me 3523 6-OMe 3-CN CO₂Me 3524 6-OMe 3-NO₂ CO₂Me 3525 6-OMe 3-OMe CO₂Me 3526 6-OMe 2-F CO₂Me 3527 6-OMe 2-Cl CO₂Me 3528 6-OMe 2-Br CO₂Me 3529 6-OMe 2-Me CO₂Me 3530 6-OMe 2-CN CO₂Me 3531 6-OMe 2-NO₂ CO₂Me 3532 6-OMe 2-OMe CO₂Me 3533 6-OMe 2,3-F₂ CO₂Me 3534 6-OMe 2,4-F₂ CO₂Me 3535 6-OMe 2,5-F₂ CO₂Me 3536 6-OMe 2,6-F₂ CO₂Me 3537 6-OMe 3,4-F₂ CO₂Me 3538 6-OMe 3,5-F₂ CO₂Me 3539 6-OMe 2,3-Cl₂ CO₂Me 3540 6-OMe 2,4-Cl₂ CO₂Me 3541 6-OMe 2,5-Cl₂ CO₂Me 3542 6-OMe 2,6-Cl₂ CO₂Me 3543 6-OMe 3,4-Cl₂ CO₂Me 3544 6-OMe 3,5-Cl₂ CO₂Me 3545 6-OMe 2-F, 3-Cl CO₂Me 3546 6-OMe 2-F, 4-Cl CO₂Me 3547 6-OMe 2-F, 5-Cl CO₂Me 3548 6-OMe 2-F, 6-Cl CO₂Me 3549 6-OMe 2,6-F₂, 4-Cl CO₂Me 3550 6-OMe 3-F, 4-Cl CO₂Me 3551 6-OMe 3-Cl, 5-F CO₂Me 3552 6-OMe 2-Cl, 5-F CO₂Me 3553 6-OMe 3-CN, 4-Cl CO₂Me 3554 6-OMe 3-NO₂, 4-Cl CO₂Me 3555 6-OMe 2-F, 4-Br CO₂Me 3556 2-F 4-F CO₂Me 3557 2-F 4-Cl CO₂Me 3558 2-F 4-Br CO₂Me 3559 2-F H CO₂Me 3560 2-F 4-Me CO₂Me 3561 2-F 4-CN CO₂Me 3562 2-F 4-NO₂ CO₂Me 3563 2-F 4-OMe CO₂Me 3564 2-F 3-F CO₂Me 3565 2-F 3-Cl CO₂Me 3566 2-F 3-Br CO₂Me 3567 2-F 3-Me CO₂Me 3568 2-F 3-CN CO₂Me 3569 2-F 3-NO₂ CO₂Me 3570 2-F 3-OMe CO₂Me 3571 2-F 2-F CO₂Me 3572 2-F 2-Cl CO₂Me 3573 2-F 2-Br CO₂Me 3574 2-F 2-Me CO₂Me 3575 2-F 2-CN CO₂Me 3576 2-F 2-NO₂ CO₂Me 3577 2-F 2-OMe CO₂Me 3578 2-F 2,3-F₂ CO₂Me 3579 2-F 2,4-F₂ CO₂Me 3580 2-F 2,5-F₂ CO₂Me 3581 2-F 2,6-F₂ CO₂Me 3582 2-F 3,4-F₂ CO₂Me 3583 2-F 3,5-F₂ CO₂Me 3584 2-F 2,3-Cl₂ CO₂Me 3585 2-F 2,4-Cl₂ CO₂Me 3586 2-F 2,5-Cl₂ CO₂Me 3587 2-F 2,6-Cl₂ CO₂Me 3588 2-F 3,4-Cl₂ CO₂Me 3589 2-F 3,5-Cl₂ CO₂Me 3590 2-F 2-F, 3-Cl CO₂Me 3591 2-F 2-F, 4-Cl CO₂Me 3592 2-F 2-F, 5-Cl CO₂Me 3593 2-F 2-F, 6-Cl CO₂Me 3594 2-F 2,6-F₂, 4-Cl CO₂Me 3595 2-F 3-F, 4-Cl CO₂Me 3596 2-F 3-Cl, 5-F CO₂Me 3597 2-F 2-Cl, 5-F CO₂Me 3598 2-F 3-CN, 4-Cl CO₂Me 3599 2-F 3-NO₂, 4-Cl CO₂Me 3600 2-F 2-F, 4-Br CO₂Me 3601 4-F 4-F CO₂Me 3602 4-F 4-Cl CO₂Me 3603 4-F 4-Br CO₂Me 3604 4-F H CO₂Me 3605 4-F 4-Me CO₂Me 3606 4-F 4-CN CO₂Me 3607 4-F 4-NO₂ CO₂Me 3608 4-F 4-OMe CO₂Me 3609 4-F 3-F CO₂Me 3610 4-F 3-Cl CO₂Me 3611 4-F 3-Br CO₂Me 3612 4-F 3-Me CO₂Me 3613 4-F 3-CN CO₂Me 3614 4-F 3-NO₂ CO₂Me 3615 4-F 3-OMe CO₂Me 3616 4-F 2-F CO₂Me 3617 4-F 2-Cl CO₂Me 3618 4-F 2-Br CO₂Me 3619 4-F 2-Me CO₂Me 3620 4-F 2-CN CO₂Me 3621 4-F 2-NO₂ CO₂Me 3622 4-F 2-OMe CO₂Me 3623 4-F 2,3-F₂ CO₂Me 3624 4-F 2,4-F₂ CO₂Me 3625 4-F 2,5-F₂ CO₂Me 3626 4-F 2,6-F₂ CO₂Me 3627 4-F 3,4-F₂ CO₂Me 3628 4-F 3,5-F₂ CO₂Me 3629 4-F 2,3-Cl₂ CO₂Me 3630 4-F 2,4-Cl₂ CO₂Me 3631 4-F 2,5-Cl₂ CO₂Me 3632 4-F 2,6-Cl₂ CO₂Me 3633 4-F 3,4-Cl₂ CO₂Me 3634 4-F 3,5-Cl₂ CO₂Me 3635 4-F 2-F, 3-Cl CO₂Me 3636 4-F 2-F, 4-Cl CO₂Me 3637 4-F 2-F, 5-Cl CO₂Me 3638 4-F 2-F, 6-Cl CO₂Me 3639 4-F 2,6-F₂, 4-Cl CO₂Me 3640 4-F 3-F, 4-Cl CO₂Me 3641 4-F 3-Cl, 5-F CO₂Me 3642 4-F 2-Cl, 5-F CO₂Me 3643 4-F 3-CN, 4-Cl CO₂Me 3644 4-F 3-NO₂, 4-Cl CO₂Me 3645 4-F 2-F, 4-Br CO₂Me 3646 2-Cl 4-F CO₂Me 3647 2-Cl 4-Cl CO₂Me 3648 2-Cl 4-Br CO₂Me 3649 2-Cl H CO₂Me 3650 2-Cl 4-Me CO₂Me 3651 2-Cl 4-CN CO₂Me 3652 2-Cl 4-NO₂ CO₂Me 3653 2-Cl 4-OMe CO₂Me 3654 2-Cl 3-F CO₂Me 3655 2-Cl 3-Cl CO₂Me 3656 2-Cl 3-Br CO₂Me 3657 2-Cl 3-Me CO₂Me 3658 2-Cl 3-CN CO₂Me 3659 2-Cl 3-NO₂ CO₂Me 3660 2-Cl 3-OMe CO₂Me 3661 2-Cl 2-F CO₂Me 3662 2-Cl 2-Cl CO₂Me 3663 2-Cl 2-Br CO₂Me 3664 2-Cl 2-Me CO₂Me 3665 2-Cl 2-CN CO₂Me 3666 2-Cl 2-NO₂ CO₂Me 3667 2-Cl 2-OMe CO₂Me 3668 2-Cl 2,3-F₂ CO₂Me 3669 2-Cl 2,4-F₂ CO₂Me 3670 2-Cl 2,5-F₂ CO₂Me 3671 2-Cl 2,6-F₂ CO₂Me 3672 2-Cl 3,4-F₂ CO₂Me 3673 2-Cl 3,5-F₂ CO₂Me 3674 2-Cl 2,3-Cl₂ CO₂Me 3675 2-Cl 2,4-Cl₂ CO₂Me 3676 2-Cl 2,5-Cl₂ CO₂Me 3677 2-Cl 2,6-Cl₂ CO₂Me 3678 2-Cl 3,4-Cl₂ CO₂Me 3679 2-Cl 3,5-Cl₂ CO₂Me 3680 2-Cl 2-F, 3-Cl CO₂Me 3681 2-Cl 2-F, 4-Cl CO₂Me 3682 2-Cl 2-F, 5-Cl CO₂Me 3683 2-Cl 2-F, 6-Cl CO₂Me 3684 2-Cl 2,6-F₂, 4-Cl CO₂Me 3685 2-Cl 3-F, 4-Cl CO₂Me 3686 2-Cl 3-Cl, 5-F CO₂Me 3687 2-Cl 2-Cl, 5-F CO₂Me 3688 2-Cl 3-CN, 4-Cl CO₂Me 3689 2-Cl 3-NO₂, 4-Cl CO₂Me 3690 2-Cl 2-F, 4-Br CO₂Me 3691 4-Cl 4-F CO₂Me 3692 4-Cl 4-Cl CO₂Me 3693 4-Cl 4-Br CO₂Me 3694 4-Cl H CO₂Me 3695 4-Cl 4-Me CO₂Me 3696 4-Cl 4-CN CO₂Me 3697 4-Cl 4-NO₂ CO₂Me 3698 4-Cl 4-OMe CO₂Me 3699 4-Cl 3-F CO₂Me 3700 4-Cl 3-Cl CO₂Me 3701 4-Cl 3-Br CO₂Me 3702 4-Cl 3-Me CO₂Me 3703 4-Cl 3-CN CO₂Me 3704 4-Cl 3-NO₂ CO₂Me 3705 4-Cl 3-OMe CO₂Me 3706 4-Cl 2-F CO₂Me 3707 4-Cl 2-Cl CO₂Me 3708 4-Cl 2-Br CO₂Me 3709 4-Cl 2-Me CO₂Me 3710 4-Cl 2-CN CO₂Me 3711 4-Cl 2-NO₂ CO₂Me 3712 4-Cl 2-OMe CO₂Me 3713 4-Cl 2,3-F₂ CO₂Me 3714 4-Cl 2,4-F₂ CO₂Me 3715 4-Cl 2,5-F₂ CO₂Me 3716 4-Cl 2,6-F₂ CO₂Me 3717 4-Cl 3,4-F₂ CO₂Me 3718 4-Cl 3,5-F₂ CO₂Me 3719 4-Cl 2,3-Cl₂ CO₂Me 3720 4-Cl 2,4-Cl₂ CO₂Me 3721 4-Cl 2,5-Cl₂ CO₂Me 3722 4-Cl 2,6-Cl₂ CO₂Me 3723 4-Cl 3,4-Cl₂ CO₂Me 3724 4-Cl 3,5-Cl₂ CO₂Me 3725 4-Cl 2-F, 3-Cl CO₂Me 3726 4-Cl 2-F, 4-Cl CO₂Me 3727 4-Cl 2-F, 5-Cl CO₂Me 3728 4-Cl 2-F, 6-Cl CO₂Me 3729 4-Cl 2,6-F₂, 4-Cl CO₂Me 3730 4-Cl 3-F, 4-Cl CO₂Me 3731 4-Cl 3-Cl, 5-F CO₂Me 3732 4-Cl 2-Cl, 5-F CO₂Me 3733 4-Cl 3-CN, 4-Cl CO₂Me 3734 4-Cl 3-NO₂, 4-Cl CO₂Me 3735 4-Cl 2-F, 4-Br CO₂Me 3736 6-OCF₂H 4-F CO₂Me 3737 6-OCF₂H 4-Cl CO₂Me 3738 6-OCF₂H 4-Br CO₂Me 3739 6-OCF₂H H CO₂Me 3740 6-OCF₂H 4-Me CO₂Me 3741 6-OCF₂H 4-CN CO₂Me 3742 6-OCF₂H 4-NO₂ CO₂Me 3743 6-OCF₂H 4-OMe CO₂Me 3744 6-OCF₂H 3-F CO₂Me 3745 6-OCF₂H 3-Cl CO₂Me 3746 6-OCF₂H 3-Br CO₂Me 3747 6-OCF₂H 3-Me CO₂Me 3748 6-OCF₂H 3-CN CO₂Me 3749 6-OCF₂H 3-NO₂ CO₂Me 3750 6-OCF₂H 3-OMe CO₂Me 3751 6-OCF₂H 2-F CO₂Me 3752 6-OCF₂H 2-Cl CO₂Me 3753 6-OCF₂H 2-Br CO₂Me 3754 6-OCF₂H 2-Me CO₂Me 3755 6-OCF₂H 2-CN CO₂Me 3756 6-OCF₂H 2-NO₂ CO₂Me 3757 6-OCF₂H 2-OMe CO₂Me 3758 6-OCF₂H 2,3-F₂ CO₂Me 3759 6-OCF₂H 2,4-F₂ CO₂Me 3760 6-OCF₂H 2,5-F₂ CO₂Me 3761 6-OCF₂H 2,6-F₂ CO₂Me 3762 6-OCF₂H 3,4-F₂ CO₂Me 3763 6-OCF₂H 3,5-F₂ CO₂Me 3764 6-OCF₂H 2,3-Cl₂ CO₂Me 3765 6-OCF₂H 2,4-Cl₂ CO₂Me 3766 6-OCF₂H 2,5-Cl₂ CO₂Me 3767 6-OCF₂H 2,6-Cl₂ CO₂Me 3768 6-OCF₂H 3,4-Cl₂ CO₂Me 3769 6-OCF₂H 3,5-Cl₂ CO₂Me 3770 6-OCF₂H 2-F, 3-Cl CO₂Me 3771 6-OCF₂H 2-F, 4-Cl CO₂Me 3772 6-OCF₂H 2-F, 5-Cl CO₂Me 3773 6-OCF₂H 2-F, 6-Cl CO₂Me 3774 6-OCF₂H 2,6-F₂, 4-Cl CO₂Me 3775 6-OCF₂H 3-F, 4-Cl CO₂Me 3776 6-OCF₂H 3-Cl, 5-F CO₂Me 3777 6-OCF₂H 2-Cl, 5-F CO₂Me 3778 6-OCF₂H 3-CN, 4-Cl CO₂Me 3779 6-OCF₂H 3-NO₂, 4-Cl CO₂Me 3780 6-OCF₂H 2-F, 4-Br CO₂Me 3781 H 3-F, 4-OMe F 3782 H 3-F, 4-OMe Cl 3783 H 3-F, 4-OMe Br 3784 H 3-F, 4-OMe Me 3785 H 3-F, 4-OMe CN 3786 H 3-F, 4-OMe NO₂ 3787 H 3-F, 4-OMe CO₂Me 3788 6-F 3-F, 4-OMe F 3789 6-F 3-F, 4-OMe Cl 3790 6-F 3-F, 4-OMe Br 3791 6-F 3-F, 4-OMe Me 3792 6-F 3-F, 4-OMe CN 3793 6-F 3-F, 4-OMe NO₂ 3794 6-F 3-F, 4-OMe CO₂Me 3795 H 3-F, 4-CN F 3796 H 3-F, 4-CN Cl 3797 H 3-F, 4-CN Br 3798 H 3-F, 4-CN Me 3799 H 3-F, 4-CN CN 3800 H 3-F, 4-CN NO₂ 3801 H 3-F, 4-CN CO₂Me 3802 6-F 3-F, 4-CN F 3803 6-F 3-F, 4-CN Cl 3804 6-F 3-F, 4-CN Br 3805 6-F 3-F, 4-CN Me 3806 6-F 3-F, 4-CN CN 3807 6-F 3-F, 4-CN NO₂ 3808 6-F 3-F, 4-CN CO₂Me 3809 6-Cl 3-F, 4-CN F 3810 6-Cl 3-F, 4-CN Cl 3811 6-Cl 3-F, 4-CN Br 3812 6-Cl 3-F, 4-CN Me 3813 6-Cl 3-F, 4-CN CN 3814 6-Cl 3-F, 4-CN NO₂ 3815 6-Cl 3-F, 4-CN CO₂Me 3816 6-CN 3-F, 4-CN F 3817 6-CN 3-F, 4-CN Cl 3818 6-CN 3-F, 4-CN Br 3819 6-CN 3-F, 4-CN Me 3820 6-CN 3-F, 4-CN CN 3821 6-CN 3-F, 4-CN NO₂ 3822 6-CN 3-F, 4-CN CO₂Me 3823 H 3-F, 4-NO₂ F 3824 H 3-F, 4-NO₂ Cl 3825 H 3-F, 4-NO₂ Br 3826 H 3-F, 4-NO₂ Me 3827 H 3-F, 4-NO₂ CN 3828 H 3-F, 4-NO₂ NO₂ 3829 H 3-F, 4-NO₂ CO₂Me 3830 6-F 3-F, 4-NO₂ F 3831 6-F 3-F, 4-NO₂ Cl 3832 6-F 3-F, 4-NO₂ Br 3833 6-F 3-F, 4-NO₂ Me 3834 6-F 3-F, 4-NO₂ CN 3835 6-F 3-F, 4-NO₂ NO₂ 3836 6-F 3-F, 4-NO₂ CO₂Me 3837 6-Cl 3-F, 4-NO₂ F 3838 6-Cl 3-F, 4-NO₂ Cl 3839 6-Cl 3-F, 4-NO₂ Br 3840 6-Cl 3-F, 4-NO₂ Me 3841 6-Cl 3-F, 4-NO₂ CN 3842 6-Cl 3-F, 4-NO₂ NO₂ 3843 6-Cl 3-F, 4-NO₂ CO₂Me 3844 6-CN 3-F, 4-NO₂ F 3845 6-CN 3-F, 4-NO₂ Cl 3846 6-CN 3-F, 4-NO₂ Br 3847 6-CN 3-F, 4-NO₂ Me 3848 6-CN 3-F, 4-NO₂ CN 3849 6-CN 3-F, 4-NO₂ NO₂ 3850 6-CN 3-F, 4-NO₂ CO₂Me 3851 H 3-Cl, 4-F F 3852 H 3-Cl, 4-F Cl 3853 H 3-Cl, 4-F Br 3854 H 3-Cl, 4-F Me 3855 H 3-Cl, 4-F CN 3856 H 3-Cl, 4-F NO₂ 3857 H 3-Cl, 4-F CO₂Me 3858 6-F 3-Cl, 4-F F 3859 6-F 3-Cl, 4-F Cl 3860 6-F 3-Cl, 4-F Br 3861 6-F 3-Cl, 4-F Me 3862 6-F 3-Cl, 4-F CN 3863 6-F 3-Cl, 4-F NO₂ 3864 6-F 3-Cl, 4-F CO₂Me 3865 6-Cl 3-Cl, 4-F F 3866 6-Cl 3-Cl, 4-F Cl 3867 6-Cl 3-Cl, 4-F Br 3868 6-Cl 3-Cl, 4-F Me 3869 6-Cl 3-Cl, 4-F CN 3870 6-Cl 3-Cl, 4-F NO₂ 3871 6-Cl 3-Cl, 4-F CO₂Me 3872 6-CN 3-Cl, 4-F F 3873 6-CN 3-Cl, 4-F Cl 3874 6-CN 3-Cl, 4-F Br 3875 6-CN 3-Cl, 4-F Me 3876 6-CN 3-Cl, 4-F CN 3877 6-CN 3-Cl, 4-F NO₂ 3878 6-CN 3-Cl, 4-F CO₂Me 3879 H 3-F, 4-Br F 3880 H 3-F, 4-Br Cl 3881 H 3-F, 4-Br Br 3882 H 3-F, 4-Br Me 3883 H 3-F, 4-Br CN 3884 H 3-F, 4-Br NO₂ 3885 H 3-F, 4-Br CO₂Me 3886 6-F 3-F, 4-Br F 3887 6-F 3-F, 4-Br Cl 3888 6-F 3-F, 4-Br Br 3889 6-F 3-F, 4-Br Me 3890 6-F 3-F, 4-Br CN 3891 6-F 3-F, 4-Br NO₂ 3892 6-F 3-F, 4-Br CO₂Me 3893 6-Cl 3-F, 4-Br F 3894 6-Cl 3-F, 4-Br Cl 3895 6-Cl 3-F, 4-Br Br 3896 6-Cl 3-F, 4-Br Me 3897 6-Cl 3-F, 4-Br CN 3898 6-Cl 3-F, 4-Br NO₂ 3899 6-Cl 3-F, 4-Br CO₂Me 3900 6-CN 3-F, 4-Br F 3901 6-CN 3-F, 4-Br Cl 3902 6-CN 3-F, 4-Br Br 3903 6-CN 3-F, 4-Br Me 3904 6-CN 3-F, 4-Br CN 3905 6-CN 3-F, 4-Br NO₂ 3906 6-CN 3-F, 4-Br CO₂Me 3907 H 3-CN, 4-F F 3908 H 3-CN, 4-F Cl 3909 H 3-CN, 4-F Br 3910 H 3-CN, 4-F Me 3911 H 3-CN, 4-F CN 3912 H 3-CN, 4-F NO₂ 3913 H 3-CN, 4-F CO₂Me 3914 6-F 3-CN, 4-F F 3915 6-F 3-CN, 4-F Cl 3916 6-F 3-CN, 4-F Br 3917 6-F 3-CN, 4-F Me 3918 6-F 3-CN, 4-F CN 3919 6-F 3-CN, 4-F NO₂ 3920 6-F 3-CN, 4-F CO₂Me 3921 6-Cl 3-CN, 4-F F 3922 6-Cl 3-CN, 4-F Cl 3923 6-Cl 3-CN, 4-F Br 3924 6-Cl 3-CN, 4-F Me 3925 6-Cl 3-CN, 4-F CN 3926 6-Cl 3-CN, 4-F NO₂ 3927 6-Cl 3-CN, 4-F CO₂Me 3928 6-CN 3-CN, 4-F F 3929 6-CN 3-CN, 4-F Cl 3930 6-CN 3-CN, 4-F Br 3931 6-CN 3-CN, 4-F Me 3932 6-CN 3-CN, 4-F CN 3933 6-CN 3-CN, 4-F NO₂ 3934 6-CN 3-CN, 4-F CO₂Me 3935 H 4-CF₃ F 3936 H 4-CF₃ Cl 3937 H 4-CF₃ Br 3938 H 4-CF₃ Me 3939 H 4-CF₃ CN 3940 H 4-CF₃ NO₂ 3941 H 4-CF₃ CO₂Me 3942 6-F 4-CF₃ F 3943 6-F 4-CF₃ Cl 3944 6-F 4-CF₃ Br 3945 6-F 4-CF₃ Me 3946 6-F 4-CF₃ CN 3947 6-F 4-CF₃ NO₂ 3948 6-F 4-CF₃ CO₂Me 3949 6-Cl 4-CF₃ F 3950 6-Cl 4-CF₃ Cl 3951 6-Cl 4-CF₃ Br 3952 6-Cl 4-CF₃ Me 3953 6-Cl 4-CF₃ CN 3954 6-Cl 4-CF₃ NO₂ 3955 6-Cl 4-CF₃ CO₂Me 3956 6-CN 4-CF₃ F 3957 6-CN 4-CF₃ Cl 3958 6-CN 4-CF₃ Br 3959 6-CN 4-CF₃ Me 3960 6-CN 4-CF₃ CN 3961 6-CN 4-CF₃ NO₂ 3962 6-CN 4-CF₃ CO₂Me 3963 H 4-OCF₃ F 3964 H 4-OCF₃ Cl 3965 H 4-OCF₃ Br 3966 H 4-OCF₃ Me 3967 H 4-OCF₃ CN 3968 H 4-OCF₃ NO₂ 3969 H 4-OCF₃ CO₂Me 3970 6-F 4-OCF₃ F 3971 6-F 4-OCF₃ Cl 3972 6-F 4-OCF₃ Br 3973 6-F 4-OCF₃ Me 3974 6-F 4-OCF₃ CN 3975 6-F 4-OCF₃ NO₂ 3976 6-F 4-OCF₃ CO₂Me 3977 6-Cl 4-OCF₃ F 3978 6-Cl 4-OCF₃ Cl 3979 6-Cl 4-OCF₃ Br 3980 6-Cl 4-OCF₃ Me 3981 6-Cl 4-OCF₃ CN 3982 6-Cl 4-OCF₃ NO₂ 3983 6-Cl 4-OCF₃ CO₂Me 3984 6-CN 4-OCF₃ F 3985 6-CN 4-OCF₃ Cl 3986 6-CN 4-OCF₃ Br 3987 6-CN 4-OCF₃ Me 3988 6-CN 4-OCF₃ CN 3989 6-CN 4-OCF₃ NO₂ 3990 6-CN 4-OCF₃ CO₂Me

Definition of the Examples in Tables 2 to 2f below:

For reference purposes, specific numbers (=Example Numbers) have been assigned to the individual compounds in Tables 2 to 2f below, where the Example Number in question is composed of the number of the chemical formula assigned to the respective table and a “row number” (row number) which refers to the same number in the row of the first column of Table 1. The chemical structure of Example No. “(formula number) (row number)” is thus defined unambiguously by the formula above the respective table by formula number and row number of Table 1, for example:

The example of No. “Iba1” from Table 2 is the compound of the formula (Ib) in which R⁴=H (=hydrogen) [=formula (Iba)] and (R¹)_(m)=H, (R²)_(n)=4-F and R³=F, defined according to row 1 of Table 1.

The example of No. “Ibd1801” from Table 2 is the compound of the formula (Ib) in which R⁴=n-propyl [=formula (Ibd)] and (R¹)_(m)=6-CN, (R²)_(n)=4-F and R³=Me=CH₃, defined according to row 1801 of Table 1.

This applies correspondingly to the assignment of racemic or optically active threo stereoisomers or erythro stereoisomers. For example, for reference purposes, specific numbers (=Example Numbers) have been assigned to the compounds of Table 2a, where the number “threo-Iba (row number)” refers to the racemic mixture of the threo enantiomers having the chemical structure of the formulae (threo-1-Iba) and (threo-2-Iba), each of which has the structural combination of groups (R¹)_(m), (R²)_(n) and R³ according to the row number of Table 1.

TABLE 2 Compounds of the formulae (Ib), (Iba), (Ibb), (Ibc), (Ibd), (Ibe), (Ibf), (Ibg) (Ibh), (Ibi), (Ibj), (Ibk), (Ibl), (Ibm), (Ibn), (Ibo), (Ibp), (Ibq), (Ibr) (Ibs), (Ibt), (Ibu), (Ibv), (Ibw), (Ibx), (Iby) and (Ibz) where (R¹)_(m), (R²)_(n) and R³ are each as defined in Table 1

(Ib)

For definitions of subformulae of formula (Ib), see Table U1 below:

TABLE U1 Formula Radical R⁴ in formula (Ib) (Iba) H (hydrogen atom) (Ibb) methyl (Ibc) ethyl (Ibd) n-propyl (Ibe) isopropyl (Ibf) 2,2-difluoroethyl (Ibg) 2,2,2-trifluoroethyl (Ibh) 2-methoxyethyl (Ibi) cyclopropylmethyl (Ibj) (1-methylcyclopropyl)methyl (Ibk) allyl (Ibl) prop-2-yn-1-yl (Ibm) ethynyl (Ibn) prop-1-yn-1-yl (Ibo) benzyl (Ibp) 4-chlorobenzyl (Ibq) phenyl (Ibr) methoxymethyl (Ibs) difluoromethyl (Ibt) oxetan-3-yl (Ibu) thietan-3-yl (Ibv) 2-(phenylsulphanyl)ethyl (Ibw) 2-(phenylsulphinyl)ethyl (Ibx) 2-(ethylsulphanyl)ethyl (Iby) 2-(ethylsulphinyl)ethyl (Ibz) tetrahydrofuran-2-ylmethyl

Erythro/Threo Mixtures of the Formulae (Iba) to (Ibz):

Examples of compounds of the formulae (Iba) to (Ibz) are the compounds of the respective formulae (Iba) to (Ibz) in the form of a racemic erythro/threo mixture (ratio 70:30 to 30:70), where the structural combination of the groups (R¹)_(m), (R²)_(n) and R³ is defined according to a row number of Table 1.

The numeration is carried out according to “(formula)(row number)” without any brackets, for example Iba200=compound of the formula (Iba) having the structural combination of row 200 of Table 1.

TABLES 2a, 2b and 2c Threo, threo-1 and threo-2 compounds of the compounds of the formulae (Ib), (Iba), (Ibb), (Ibc), (Ibd), (Ibe), (Ibf), (Ibg) (Ibh), (Ibi), (Ibj), (Ibk), (Ibl), (Ibm), (Ibn), (Ibo), (Ibp), (Ibq), (Ibr) (Ibs), (Ibt), (Ibu), (Ibv), (Ibw), (Ibx), (Iby) and (Ibz) where (R¹)_(m), (R²)_(n) and R³ are each as defined in Table 1

(threo-1-Ib)

(threo-2-Ib) (threo-Ib) = (threo-1-Ib) + (threo-2-Ib) (50:50) = (rac.)

For definitions of subformulae of formulae (threo-1b), (threo-1-1b) and (threo-2-1b), see Table U2 below:

TABLE U2 Formula Radical R⁴ in formula (threo-Ib) (threo-Iba) H (hydrogen atom) (threo-1-Iba) H (hydrogen atom) (threo-2-Iba) H (hydrogen atom) (threo-Ibb) methyl (threo-1-Ibb) methyl (threo-2-Ibb) methyl (threo-Ibc) ethyl (threo-1-Ibc) ethyl (threo-2-Ibc) ethyl (threo-Ibd) n-propyl (threo-1-Ibd) n-propyl (threo-2-Ibd) n-propyl (threo-Ibe) isopropyl (threo-1-Ibe) isopropyl (threo-2-Ibe) isopropyl (threo-Ibf) 2,2-difluoroethyl (threo-1-Ibf) 2,2-difluoroethyl (threo-2-Ibf) 2,2-difluoroethyl (threo-Ibg) 2,2,2-trifluoroethyl (threo-1-Ibg) 2,2,2-trifluoroethyl (threo-2-Ibg) 2,2,2-trifluoroethyl (threo-Ibh) 2-methoxyethyl (threo-1-Ibh) 2-methoxyethyl (threo-2-Ibh) 2-methoxyethyl (threo-Ibi) cyclopropylmethyl (threo-1-Ibi) cyclopropylmethyl (threo-2-Ibi) cyclopropylmethyl (threo-Ibj) (1-methylcyclopropyl)methyl (threo-1-Ibj) (1-methylcyclopropyl)methyl (threo-2-Ibj) (1-methylcyclopropyl)methyl (threo-Ibk) allyl (threo-1-Ibk) allyl (threo-2-Ibk) allyl (threo-Ibl) prop-2-yn-1-yl (threo-1-Ibl) prop-2-yn-1-yl (threo-2-Ibl) prop-2-yn-1-yl (threo-Ibm) ethynyl (threo-1-Ibm) ethynyl (threo-2-Ibm) ethynyl (threo-Ibn) prop-1-yn-1-yl (threo-1-Ibn) prop-1-yn-1-yl (threo-2-Ibn) prop-1-yn-1-yl (threo-Ibo) benzyl (threo-1-Ibo) benzyl (threo-2-Ibo) benzyl (threo-Ibp) 4-chlorobenzyl (threo-1-Ibp) 4-chlorobenzyl (threo-2-Ibp) 4-chlorobenzyl (threo-Ibq) phenyl (threo-1-Ibq) phenyl (threo-2-Ibq) phenyl (threo-Ibr) methoxymethyl (threo-1-Ibr) methoxymethyl (threo-2-Ibr) methoxymethyl (threo-Ibs) difluoromethyl (threo-1-Ibs) difluoromethyl (threo-2-Ibs) difluoromethyl (threo-Ibt) oxetan-3-yl (threo-1-Ibt) oxetan-3-yl (threo-2-Ibt) oxetan-3-yl (threo-Ibu) thietan-3-yl (threo-1-Ibu) thietan-3-yl (threo-2-Ibu) thietan-3-yl (threo-Ibv) 2-(phenylsulphanyl)ethyl (threo-1-Ibv) 2-(phenylsulphanyl)ethyl (threo-2-Ibv) 2-(phenylsulphanyl)ethyl (threo-Ibw) 2-(phenylsulphinyl)ethyl (threo-1-Ibw) 2-(phenylsulphinyl)ethyl (threo-2-Ibw) 2-(phenylsulphinyl)ethyl (threo-Ibx) 2-(ethylsulphanyl)ethyl (threo-1-Ibx) 2-(ethylsulphanyl)ethyl (threo-2-Ibx) 2-(ethylsulphanyl)ethyl (threo-Iby) 2-(ethylsulphinyl)ethyl (threo-1-Iby) 2-(ethylsulphinyl)ethyl (threo-2-Iby) 2-(ethylsulphinyl)ethyl (threo-Ibz) tetrahydrofuran-2-ylmethyl (threo-1-Ibz) tetrahydrofuran-2-ylmethyl (threo-2-Ibz) tetrahydrofuran-2-ylmethyl

Table 2a (Threo Racemates), Examples:

Examples of the compounds of the formulae (threo-Iba) to (threo-Ibz) (see Table U2) are the compounds of the formulae in question in the form of the racemic mixture of the threo isomers where the structural combination of groups (R¹)_(m), (R²)_(n) and R³ is defined according to a row number of Table 1.

The numeration is carried out according to “(formula)(row number)” without any brackets, for example threo-Iba200=compound of the formula (threo-Iba) having the structural combination of row 200 of Table 1.

Table 2b (Optically Active Threo-2 Enantiomers): Examples:

Examples of the compounds of the formulae (threo-2-Iba) to (threo-2-Ibz) (see Table U2) are the optically active threo-2 compounds of the formulae in question in enriched form [=(3R,4R)-form having more than 90% ee] where the structural combination of groups (R¹)_(m), (R²)_(n) and R³ is defined according to a row number of Table 1.

Compounds are numbered “(formula)(row number)”, without any brackets. For example, No. threo-2-Iba1789 refers to the compound of the formula (threo-2-Iba) in which (R¹)_(m)=6-Br, (R²)_(n)=3,5-Cl₂ and R³=Me.

Table 2c (Optically Active Threo-1 Enantiomers): Examples:

Examples of the compounds of the formulae (threo-1-Iba) to (threo-1-Ibz) (see Table U2) are the optically active threo-1 compounds of the formulae in question in enriched form [=(3S,4S)-form having more than 90% ee] where the structural combination of groups (R¹)_(m), (R²)_(n) and R³ is defined according to a row number of Table 1.

Compounds are numbered “(formula)(row number)”, without any brackets. For example, No. threo-1-Ibb5 refers to the compound of the formula (threo-1-Ibb) in which (R¹)_(m)=H, (R²)_(n)=4-Me and R³=F.

TABLES 2d, 2e and 2f Erythro, erythro-1 and erythro-2 compounds of the compounds of the formulae (Ib), (Iba), (Ibb), (Ibc), (Ibd), (Ibe), (Ibf), (Ibg) (Ibh), (Ibi), (Ibj), (Ibk), (Ibl), (Ibm), (Ibn), (Ibo), (Ibp), (Ibq), (Ibr) (Ibs), (Ibt), (Ibu), (Ibv), (Ibw), (Ibx), (Iby) and (Ibz) where (R¹)_(m), (R²)_(n) and R³ are each as defined in Table 1

(erythro-1-Ib)

(erythro-2-Ib) (erythro-Ib) = (erythro-1-Ib) + (erythro-2-Ib) (50:50) = (rac.)

For definitions of subformulae of formulae (erythro-Ib), (erythro-1-Ib) and (erythro-2-Ib), see Table U3 below:

TABLE U3 Formula Radical R⁴ in formula (erythro-Ib) (erythro-Iba) H (hydrogen atom) (erythro-1-Iba) H (hydrogen atom) (erythro-2-Iba) H (hydrogen atom) (erythro-Ibb) methyl (erythro-1-Ibb) methyl (erythro-2-Ibb) methyl (erythro-Ibc) ethyl (erythro-1-Ibc) ethyl (erythro-2-Ibc) ethyl (erythro-Ibd) n-propyl (erythro-1-Ibd) n-propyl (erythro-2-Ibd) n-propyl (erythro-Ibe) isopropyl (erythro-1-Ibe) isopropyl (erythro-2-Ibe) isopropyl (erythro-Ibf) 2,2-difluoroethyl (erythro-1-Ibf) 2,2-difluoroethyl (erythro-2-Ibf) 2,2-difluoroethyl (erythro-Ibg) 2,2,2-trifluoroethyl (erythro-1-Ibg) 2,2,2-trifluoroethyl (erythro-2-Ibg) 2,2,2-trifluoroethyl (erythro-Ibh) 2-methoxyethyl (erythro-1-Ibh) 2-methoxyethyl (erythro-2-Ibh) 2-methoxyethyl (erythro-Ibi) cyclopropylmethyl (erythro-1-Ibi) cyclopropylmethyl (erythro-2-Ibi) cyclopropylmethyl (erythro-Ibj) (1-methylcyclopropyl)methyl (erythro-1-Ibj) (1-methylcyclopropyl)methyl (erythro-2-Ibj) (1-methylcyclopropyl)methyl (erythro-Ibk) allyl (erythro-1-Ibk) allyl (erythro-2-Ibk) allyl (erythro-Ibl) prop-2-yn-1-yl (erythro-1-Ibl) prop-2-yn-1-yl (erythro-2-Ibl) prop-2-yn-1-yl (erythro-Ibm) ethynyl (erythro-1-Ibm) ethynyl (erythro-2-Ibm) ethynyl (erythro-Ibn) prop-1-yn-1-yl (erythro-1-Ibn) prop-1-yn-1-yl (erythro-2-Ibn) prop-1-yn-1-yl (erythro-Ibo) benzyl (erythro-1-Ibo) benzyl (erythro-2-Ibo) benzyl (erythro-Ibp) 4-chlorobenzyl (erythro-1-Ibp) 4-chlorobenzyl (erythro-2-Ibp) 4-chlorobenzyl (erythro-Ibq) phenyl (erythro-1-Ibq) phenyl (erythro-2-Ibq) phenyl (erythro-Ibr) methoxymethyl (erythro-1-Ibr) methoxymethyl (erythro-2-Ibr) methoxymethyl (erythro-Ibs) difluoromethyl (erythro-1-Ibs) difluoromethyl (erythro-2-Ibs) difluoromethyl (erythro-Ibt) oxetan-3-yl (erythro-1-Ibt) oxetan-3-yl (erythro-2-Ibt) oxetan-3-yl (erythro-Ibu) thietan-3-yl (erythro-1-Ibu) thietan-3-yl (erythro-2-Ibu) thietan-3-yl (erythro-Ibv) 2-(phenylsulphanyl)ethyl (erythro-1-Ibv) 2-(phenylsulphanyl)ethyl (erythro-2-Ibv) 2-(phenylsulphanyl)ethyl (erythro-Ibw) 2-(phenylsulphinyl)ethyl (erythro-1-Ibw) 2-(phenylsulphinyl)ethyl (erythro-2-Ibw) 2-(phenylsulphinyl)ethyl (erythro-Ibx) 2-(ethylsulphanyl)ethyl (erythro-1-Ibx) 2-(ethylsulphanyl)ethyl (erythro-2-Ibx) 2-(ethylsulphanyl)ethyl (erythro-Iby) 2-(ethylsulphinyl)ethyl (erythro-1-Iby) 2-(ethylsulphinyl)ethyl (erythro-2-Iby) 2-(ethylsulphinyl)ethyl (erythro-Ibz) tetrahydrofuran-2-ylmethyl (erythro-1-Ibz) tetrahydrofuran-2-ylmethyl (erythro-2-Ibz) tetrahydrofuran-2-ylmethyl

Table 2d (Erythro Racemates), Examples:

Examples of the compounds of the formulae (erythro-Iba) to (erythro-Ibz) (see Table U3) are the compounds of the formulae in question in the form of the racemic mixture of the erythro isomers where the structural combination of groups (R¹)_(m), (R²)_(n) and R³ is defined according to a row number of Table 1.

The numeration is carried out according to “(formula)(row number)” without any brackets, for example erythro-Iba200=compound of the formula (erythro-Iba) having the structural combination of row 200 of Table 1.

Table 2e (Optically Active Erythro-2 Enantiomers): Examples:

Examples of the compounds of the formulae (erythro-2-Iba) to (erythro-2-Ibz) (see Table U3) are the optically active erythro-2 compounds of the formulae in question in enriched form [=(3R,4S)-form having more than 90% ee] where the structural combination of groups (R¹)_(m), (R²)_(n) and R³ is defined according to a row number of Table 1.

Compounds are numbered “(formula)(row number)”, without any brackets. For example, No. erythro-2-Iba1789 refers to the compound of the formula (erythro-2-Iba) in which (R¹)_(m)=6-Br, (R²)_(n)=3,5-Cl₂ and R³=Me.

Table 2f (Optically Active Erythro-1 Enantiomers): Examples:

Examples of the compounds of the formulae (erythro-1-Iba) to (erythro-1-Ibz) (see Table U3) are the optically active erythro-1 compounds of the formulae in question in enriched form [=(3S,4R)-form having more than 90% ee] where the structural combination of groups (R¹)_(m), (R²)_(n) and R³ is defined according to a row number of Table 1.

Compounds are numbered “(formula)(row number)”, without any brackets. For example, No. erythro-1-Ibb5 refers to the compound of the formula (erythro-1-Ibb) in which (R¹)_(m)=H, (R²)_(n)=4-Me and R³=F.

Physical Data for Tables 2a-2f:

Test Methods:

-   1) NMR=¹H-NMR data (400 MHz, CDCl₃); characteristic chemical shifts     [in ppm] are indicated for the example in question, -   2) MS=mass spectrum, measured using a quadrupole instrument;     electrospray ionization (+−), mass range 100-1000; molecular peak M     or [M+H]+ or [M−1]+ or [M−2]+ or [M+1]+ indicated for the example in     question, -   3) HPLC=High Performance Liquid Chromatography, column: Zorbax     Eclipse, 50×3.0, C18 1.8 ym, mobile phase: water+0.06% formic     acid/acrylonitrile+0.06% formic acid, gradient: 90:10, after 2 min     5:95; detector: DAD (210-400 nm); retention time (rt) indicated for     the example in question, -   4) chiral HPLC=HPLC on a chiral column, column: Chiralpak IC,     250×4.6 mm, 5 μm DAIC 83325, detector wavelength: 210 nm; column     temperature 25° C., -    mobile phase a: (n-heptane:2-propanol), (60:40), Chromasolv, flow     rate: 1.0 ml/min -    mobile phase b: (n-heptane:2-propanol), (70:30), Chromasolv, flow     rate: 1.0 ml/min -    mobile phase c: (n-heptane:2-propanol), (80:20), Chromasolv, flow     rate: 1.0 ml/min -    mobile phase d: (n-heptane:2-propanol), (90:10), Chromasolv, flow     rate: 0.6 ml/min

Ex. erythro-Ibb2, NMR: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.53 (m, 1H), 3.71 (s, 3H), 4.56 (d, 1H), 6.95 (d, 2H), 7.08 (dt, 1H), 7.25 (d, 2H), 8.24 (bs, 1H), 8.43 (d, 1H)

Ex. erythro-1-Ibb2, NMR: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.53 (m, 1H), 3.71 (s, 3H), 4.56 (d, 1H), 6.95 (d, 2H), 7.08 (dt, 1H), 7.25 (d, 2H), 8.24 (bs, 1H), 8.43 (d, 1H)); chiral HPLC: 29.9 min, mobile phase d

Ex. erythro-2-Ibb2, NMR: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.53 (m, 1H), 3.71 (s, 3H), 4.56 (d, 1H), 6.95 (d, 2H), 7.08 (dt, 1H), 7.25 (d, 2H), 8.24 (bs, 1H), 8.43 (d, 1H)); chiral HPLC: 32.9 min, mobile phase d

Ex. threo-Ibb2, NMR: 2.92 (m, 2H), 3.60 (s, 3H), 3.66 (q, 1H), 4.18 (d, 1H), 7.04 (d, 2H), 7.25 (dt, 1H), 7.28 (d, 2H), 8.15 (bs, 1H), 8.44 (d, 1H)

Ex. threo-1-Ibb2, NMR: 2.92 (m, 2H), 3.60 (s, 3H), 3.66 (q, 1H), 4.18 (d, 1H), 7.04 (d, 2H), 7.25 (dt, 1H), 7.28 (d, 2H), 8.15 (bs, 1H), 8.44 (d, 1H)); chiral HPLC: 11.7 min, mobile phase c

Ex. threo-2-Ibb2, NMR: 2.92 (m, 2H), 3.60 (s, 3H), 3.66 (q, 1H), 4.18 (d, 1H), 7.04 (d, 2H), 7.25 (dt, 1H), 7.28 (d, 2H), 8.15 (bs, 1H), 8.44 (d, 1H)); chiral HPLC: 23.2 min, mobile phase c

Ex. erythro-Ibb4, NMR: 2.89 (dd, 1H), 3.10 (dd, 1H), 3.53 (m, 1H), 3.71 (s, 3H), 4.57 (d, 1H), 7.01 (m, 3H), 8.22 (m, 1H), 8.40 (d, 1H)

Ex. threo-Ibb4, NMR: 2.94 (d, 2H), 3.59 (s, 3H), 3.66 (q, 1H), 4.20 (d, 1H), 7.07 (m, 2H), 7.20 (m, 1H), 8.14 (m, 1H), 8.40 (d, 1H)

Ex. erythro-Ibb7, NMR: 2.90 (dd, 1H), 3.11 (dd, 1H), 3.69 (m, 1H), 3.71 (s, 3H), 4.62 (d, 1H), 7.12 (dt, 1H), 7.23 (d, 2H), 8.15 (d, 2H), 8.27 (bs, 1H), 8.46 (d, 1H)

Ex. threo-Ibb7, NMR: 2.98 (d, 2H), 3.60 (s, 3H), 3.80 (q, 1H), 4.25 (d, 1H), 7.32 (m, 1H), 7.33 (d, 2H), 8.19 (d, 2H), 8.19 (m, 1H), 8.44 (bs, 1H)

Ex. erythro-Ibb9, NMR: 2.87 (dd, 1H), 3.06 (dd, 1H), 3.54 (m, 1H), 3.71 (s, 3H), 4.56 (d, 1H), 6.78 (m, 2H), 7.00 (m, 1H), 7.08 (t, 1H), 8.25 (m, 1H), 8.43 (d, 1H)

Ex. threo-Ibb9, NMR: 2.93 (m, 2H), 3.60 (s, 3H), 3.66 (q, 1H), 4.19 (d, 1H), 6.83 (m, 1H), 6.88 (d, 1H), 6.98 (m. 1H), 8.17 (t, 1H), 8.43 (d, 1H)

Ex. threo-Ibb10, NMR: 2.93 (d, 2H), 3.61 (s, 3H), 3.64 (q, 1H), 4.19 (d, 1H), 6.99 (m, 1H), 7.09 (m, 1H), 8.17 (bs, 1H), 8.44 (d, 1H)

Ex. erythro-Ibb25, NMR: 2.81 (dd, 1H), 3.00 (dd, 1H), 3.70 (s, 3H), 3.96 (q, 1H), 4.59 (d, 1H), 6.91 (m, 1H), 6.99 (m, 1H), 7.11 (m, 1H), 7.21 (dt, 1H), 8.28 (bs, 1H), 8.45 (d, 1H)

Ex. threo-Ibb25, NMR: 3.00 (m, 2H), 3.60 (s, 3H), 3.91 (q, 1H), 4.26 (d, 1H), 6.85 (m, 1H), 7.00 (m. 2H), 7.40 (dt, 1H), 8.25 (bs, 1H), 8.44 (d, 1H)

Ex. erythro-Ibb26, NMR: 2.88 (d, 2H), 3.59 (s, 3H), 4.11 (q, 1H), 4.46 (d, 1H), 6.92 (t, 2H), 7.44 (dt, 1H), 8.39 (bs, 1H), 8.49 (d, 1H)

Ex. erythro-1-Ibb26, NMR: 2.88 (d, 2H), 3.59 (s, 3H), 4.11 (q, 1H), 4.46 (d, 1H), 6.92 (t, 2H), 7.44 (dt, 1H), 8.39 (bs, 1H), 8.49 (d, 1H); chiral HPLC: 12.5 min, mobile phase c

Ex. erythro-2-Ibb26, NMR: 2.88 (d, 2H), 3.59 (s, 3H), 4.11 (q, 1H), 4.46 (d, 1H), 6.92 (t, 2H), 7.44 (dt, 1H), 8.39 (bs, 1H), 8.49 (d, 1H); chiral HPLC: 13.5 min, mobile phase c

Ex. threo-Ibb26, NMR: 3.15 (dd, 1H), 3.23 (dd, 1H), 3.63 (s, 3H), 4.17 (m, 1H), 4.26 (d, 1H), 6.78 (t, 2H), 7.39 (dt, 1H), 8.10 (bs, 1H), 8.36 (bs, 1H)

Ex. threo-1-Ibb26, NMR: 3.15 (dd, 1H), 3.23 (dd, 1H), 3.63 (s, 3H), 4.17 (m, 1H), 4.26 (d, 1H), 6.78 (t, 2H), 7.39 (dt, 1H), 8.10 (bs, 1H), 8.36 (bs, 1H); chiral HPLC: 11.7 min, mobile phase c

Ex. threo-2-Ibb26, NMR: 3.15 (dd, 1H), 3.23 (dd, 1H), 3.63 (s, 3H), 4.17 (m, 1H), 4.26 (d, 1H), 6.78 (t, 2H), 7.39 (dt, 1H), 8.10 (bs, 1H), 8.36 (bs, 1H); chiral HPLC: 16.5 min, mobile phase c

Ex. erythro-Ibb541, NMR: 2.86 (dd, 1H), 3.06 (dd, 1H), 3.52 (m, 1H), 3.71 (s, 3H), 4.50 (d, 1H), 6.98 (d, 2H), 7.32 (t, 1H), 8.24 (d, 1H), 8.52 (d, 1H)

Ex. threo-Ibb541, NMR: 2.90 (m, 2H), 3.60 (s, 3H), 3.66 (q, 1H), 4.14 (d, 1H), 7.00 (m, 2H), 7.06 (m, 2H), 7.48 (t, 1H), 8.18 (d, 1H), 8.52 (d, 1H)

Ex. erythro-Ibb542, NMR: 2.85 (dd, 1H), 3.05 (dd, 1H), 3.51 (m, 1H), 3.70 (s, 3H), 4.50 (d, 1H), 6.95 (d, 2H), 7.27 (d, 2H), 7.35 (t, 1H), 8.25 (d, 1H), 8.52 (d, 1H)

Ex. threo-Ibb542, NMR: 2.89 (d, 2H), 3.60 (s, 3H), 3.64 (q, 1H), 4.14 (d, 1H), 7.04 (d, 2H), 7.29 (d, 2H), 7.50 (t, 1H), 8.19 (d, 1H), 8.53 (d, 1H)

Ex. threo-1-Ibb542, NMR: 2.89 (d, 2H), 3.60 (s, 3H), 3.64 (q, 1H), 4.14 (d, 1H), 7.04 (d, 2H), 7.29 (d, 2H), 7.50 (t, 1H), 8.19 (d, 1H), 8.53 (d, 1H); chiral HPLC: 11.0 min, mobile phase c

Ex. threo-2-Ibb542, NMR: 2.89 (d, 2H), 3.60 (s, 3H), 3.64 (q, 1H), 4.14 (d, 1H), 7.04 (d, 2H), 7.29 (d, 2H), 7.50 (t, 1H), 8.19 (d, 1H), 8.53 (d, 1H); chiral HPLC: 18.5 min, mobile phase c

Ex. erythro-Ibb543, NMR: 2.85 (dd, 1H), 3.05 (dd, 1H), 3.50 (m, 1H), 3.70 (s, 3H), 4.50 (d, 1H), 6.89 (d, 2H), 7.36 (s, 1H), 7.42 (d, 2H), 8.25 (s, 1H), 8.53 (s, 1H)

Ex. threo-Ibb543, NMR: 2.90 (d, 2H), 3.60 (s, 3H), 3.63 (q, 1H), 4.14 (d, 1H), 6.98 (d, 2H), 7.44 (d, 2H), 7.51 (t, 1H), 8.19 (d, 1H), 8.53 (d, 1H)

Ex. erythro-Ibb544, NMR: 2.89 (dd, 1H), 3.10 (dd, 1H), 3.52 (m, 1H), 3.70 (s, 3H), 4.52 (d, 1H), 7.00 (m, 2H), 7.29 (m, 4H), 8.23 (d, 1H), 8.50 (d, 1H)

Ex. threo-Ibb544, NMR: 2.94 (d, 2H), 3.59 (s, 3H), 3.65 (q, 1H), 4.16 (d, 1H), 7.07 (m, 2H), 7.29 (m, 3H), 7.45 (t, 1H), 8.16 (d, 1H), 8.60 (d, 1H)

Ex. erythro-Ibb546, NMR: 2.87 (dd, 1H), 3.08 (dd, 1H), 3.60 (m, 1H), 3.71 (s, 3H), 4.55 (d, 1H), 7.15 (d, 2H), 7.35 (t, 1H), 7.60 (d, 2H), 8.27 (d, 1H), 8.55 (d, 1H)

Ex. threo-Ibb546, NMR: 2.94 (d, 2H), 3.60 (s, 3H), 3.73 (q, 1H), 4.18 (d, 1H), 7.26 (d, 2H), 7.51 (t, 1H), 7.63 (d, 2H), 8.21 (bs, 1H), 8.55 (bs, 1H)

Ex. erythro-Ibb547, NMR: 2.90 (dd, 1H), 3.10 (dd, 1H), 3.68 (m, 1H), 3.71 (s, 3H), 4.57 (d, 1H), 7.22 (d, 2H), 7.40 (t, 1H), 8.17 (d, 2H), 8.28 (d, 1H), 8.55 (d, 1H)

Ex. threo-Ibb547, NMR: 2.97 (d, 2H), 3.60 (s, 3H), 3.80 (q, 1H), 4.21 (d, 1H), 7.34 (d, 2H), 7.55 (t, 1H), 8.20 (d, 2H), 8.23 (bs, 1H), 8.56 (bs, 1H)

Ex. erythro-Ibb548, NMR: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.47 (m, 1H), 3.70 (s, 3H), 3.78 (s, 3H), 4.47 (d, 1H), 6.80 (d, 2H), 6.91 (d, 2H), 7.31 (m, 1H), 8.22 (d, 1H), 8.50 (d, 1H)

Ex. threo-Ibb548, NMR: 2.89 (m, 2H), 3.59 (s, 3H), 3.60 (m, 1H), 3.78 (s, 3H), 4.12 (d, 1H), 6.81 (d, 2H), 6.98 (d, 2H), 7.46 (t, 1H), 8.15 (d, 1H), 8.50 (d, 1H)

Ex. erythro-Ibb553, NMR: 2.87 (dd, 1H), 3.07 (dd, 1H), 3.58 (m, 1H), 3.71 (s, 3H), 4.53 (d, 1H), 7.31 (m, 2H), 7.36 (t, 1H), 7.44 (t, 1H), 7.62 (m, 1H), 8.27 (d, 1H), 8.55 (d, 1H)

Ex. threo-Ibb553, NMR: 2.93 (d, 2H), 3.61 (s, 3H), 3.71 (q, 1H), 4.17 (d, 1H), 7.41 (m, 2H), 7.46 (t, 1H), 7.51 (t, 1H), 7.62 (m, 1H), 8.21 (d, 1H), 8.55 (d, 1H)

Ex. erythro-Ibb565, NMR: 2.81 (dd, 1H), 2.99 (dd, 1H), 3.69 (s, 3H), 3.94 (q, 1H), 4.54 (d, 1H), 6.93 (m, 1H), 6.99 (m, 1H), 7.10 (m, 1H), 7.45 (t, 1H), 8.31 (bs, 1H), 8.54 (d, 1H)

Ex. threo-Ibb565, NMR: 2.99 (m, 2H), 3.60 (s, 3H), 3.91 (q, 1H), 4.22 (d, 1H), 6.86 (m, 1H), 6.98 (m. 1H), 7.01 (m, 1H), 7.65 (t, 1H), 8.30 (d, 1H), 8.53 (d, 1H)

Ex. erythro-Ibb566, NMR: 2.88 (d, 2H), 3.59 (s, 3H), 4.10 (q, 1H), 4.41 (d, 1H), 6.92 (t, 2H), 7.32 (m, 1H), 7.69 (t, 1H), 8.44 (bs, 1H), 8.59 (bs, 1H)

Ex. threo-Ibb566, NMR: 3.12 (dd, 1H), 3.23 (dd, 1H), 3.63 (s, 3H), 4.18 (m, 1H), 4.22 (d, 1H), 6.79 (t, 2H), 7.18 (m, 1H), 7.64 (t, 1H), 8.15 (d, 1H), 8.45 (d, 1H)

Ex. threo-1-Ibb566, NMR: 3.12 (dd, 1H), 3.23 (dd, 1H), 3.63 (s, 3H), 4.18 (m, 1H), 4.22 (d, 1H), 6.79 (t, 2H), 7.18 (m, 1H), 7.64 (t, 1H), 8.15 (d, 1H), 8.45 (d, 1H)); chiral HPLC: 11.5 min, mobile phase c

Ex. threo-2-Ibb566, NMR: 3.12 (dd, 1H), 3.23 (dd, 1H), 3.63 (s, 3H), 4.18 (m, 1H), 4.22 (d, 1H), 6.79 (t, 2H), 7.18 (m, 1H), 7.64 (t, 1H), 8.15 (d, 1H), 8.45 (d, 1H)); chiral HPLC: 15.4 min, mobile phase c

Ex. Ibb587 (erythro-Ibb587: threo-Ibb587=50:50), NMR:

erythro-Ibb587: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.48 (m, 1H), 3.71 (s, 3H), 4.53 (d, 1H), 6.96 (d, 2H), 7.28 (d, 2H), 7.46 (dd, 1H), 7.83 (m, 1H)

threo-Ibb587: 2.89 (m, 2H), 3.61 (s, 3H), 3.63 (q, 1H), 4.16 (d, 1H), 7.03 (d, 2H), 7.30 (d, 2H), 7.61 (dd, 1H), 7.77 (m, 1H)

Ex. erythro-Ibb587: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.48 (m, 1H), 3.71 (s, 3H), 4.53 (d, 1H), 6.96 (d, 2H), 7.28 (d, 2H), 7.46 (dd, 1H), 7.83 (m, 1H)

Ex. threo-Ibb587: 2.89 (m, 2H), 3.61 (s, 3H), 3.63 (q, 1H), 4.16 (d, 1H), 7.03 (d, 2H), 7.30 (d, 2H), 7.61 (dd, 1H), 7.77 (m, 1H)

Ex. Ibb589 (erythro-Ibb589: threo-Ibb589=50:50), NMR:

erythro-Ibb589: 2.90 (dd, 1H), 3.11 (dd, 1H), 3.48 (m, 1H), 3.71 (s, 3H), 4.55 (d, 1H), 7.00 (m, 2H), 7.30 (m, 3H), 7.37 (dd, 1H), 7.81 (m, 1H)

threo-Ibb589: 2.94 (m, 2H), 3.61 (s, 3H), 3.63 (q, 1H), 4.17 (d, 1H), 7.05 (m, 2H), 7.54 (dd, 1H), 7.74 (m, 1H)

Ex. erythro-Ibb589: 2.90 (dd, 1H), 3.11 (dd, 1H), 3.48 (m, 1H), 3.71 (s, 3H), 4.55 (d, 1H), 7.00 (m, 2H), 7.30 (m, 3H), 7.37 (dd, 1H), 7.81 (m, 1H)

Ex. erythro-Ibb592: 2.90 (dd, 1H), 3.10 (dd, 1H), 3.65 (m, 1H), 3.72 (s, 3H), 4.59 (d, 1H), 7.25 (d, 2H), 7.53 (dd, 1H), 7.87 (m, 1H), 8.18 (d, 2H)

Ex. threo-Ibb592: 2.97 (d, 2H), 3.61 (s, 3H), 3.78 (q, 1H), 4.23 (d, 1H), 7.33 (d, 2H), 7.68 (dd, 1H), 7.82 (m, 1H), 8.20 (d, 2H)

Ex. Ibb594 (erythro-Ibb594: threo-Ibb594=54:46), NMR:

erythro-Ibb594: 2.87 (dd, 1H), 3.06 (dd, 1H), 3.50 (m, 1H), 3.72 (s, 3H), 4.54 (d, 1H), 6.79 (m, 2H), 7.00 (m, 1H), 7.28 (m, 1H), 7.45 (dd, 1H), 7.85 (m, 1H)

threo-Ibb594: 2.92 (m, 2H), 3.62 (s, 3H), 3.63 (q, 1H), 4.17 (d, 1H), 6.83 (m, 2H), 7.01 (m, 1H), 7.28 (m, 1H), 7.61 (dd, 1H), 7.78 (m, 1H)

Ex. erythro-Ibb594: 2.87 (dd, 1H), 3.06 (dd, 1H), 3.50 (m, 1H), 3.72 (s, 3H), 4.54 (d, 1H), 6.79 (m, 2H), 7.00 (m, 1H), 7.28 (m, 1H), 7.45 (dd, 1H), 7.85 (m, 1H)

Ex. Ibb595 (erythro-Ibb595: threo-Ibb595=48:52), NMR:

erythro-Ibb595: 2.85 (dd, 1H), 3.05 (dd, 1H), 3.47 (m, 1H), 3.71 (s, 3H), 4.53 (d, 1H), 6.91 (dt, 1H), 7.04 (t, 1H), 7.45 (dd, 1H), 7.86 (m, 1H)

threo-Ibb595: 2.91 (m, 2H), 3.61 (q, 1H), 3.62 (s, 3H), 4.18 (d, 1H), 6.98 (dt, 1H), 7.10 (t, 1H), 7.62 (dd, 1H), 7.80 (m, 1H)

Ex. erythro-Ibb595: 2.85 (dd, 1H), 3.05 (dd, 1H), 3.47 (m, 1H), 3.71 (s, 3H), 4.53 (d, 1H), 6.91 (dt, 1H), 7.04 (t, 1H), 7.24 (t, 1H), 7.30 (m, 1H), 7.45 (dd, 1H), 7.86 (m, 1H)

Ex. Ibb610 (erythro-Ibb610: threo-Ibb610=55:45), NMR:

erythro-Ibb610: 2.82 (dd, 1H), 3.01 (dd, 1H), 3.71 (s, 3H), 3.93 (m, 1H), 4.58 (d, 1H), 6.94 (m, 1H), 6.99 (m, 1H), 7.12 (m, 1H), 7.59 (dd, 1H), 7.90 (m, 1H)

threo-Ibb610: 2.99 (m, 2H), 3.61 (s, 3H), 3.90 (q, 1H), 4.22 (d, 1H), 6.86 (m, 1H), 7.00 (m, 2H), 7.79 (m, 1H), 7.88 (m, 2H)

Ex. erythro-Ibb610: 2.82 (dd, 1H), 3.01 (dd, 1H), 3.71 (s, 3H), 3.93 (m, 1H), 4.58 (d, 1H), 6.94 (m, 1H), 6.99 (m, 1H), 7.12 (m, 1H), 7.59 (dd, 1H), 7.90 (m, 1H)

Ex. Ibb611 (erythro-Ibb611: threo-Ibb611=50:50), NMR:

erythro-Ibb611: 2.88 (dd, 1H), 2.93 (dd, 1H), 3.62 (s, 3H), 4.07 (q, 1H), 4.45 (d, 1H), 6.92 (t, 2H), 7.31 (m, 1H), 7.81 (dd, 1H), 8.02 (m, 1H)

threo-Ibb611: 3.11 (dd, 1H), 3.24 (dd, 1H), 3.63 (s, 3H), 4.16 (m, 1H), 4.22 (d, 1H), 6.81 (t, 2H), 7.23 (m, 1H), 7.74 (m, 1H), 7.78 (dd, 1H)

Ex. erythro-Ibb624: 2.87 (m, 2H), 3.63 (s, 3H), 4.01 (q, 1H), 4.40 (d, 1H), 6.98 (d, 2H), 7.84 (dd, 1H), 8.03 (m, 1H)

Ex. threo-Ibb624: 3.07 (dd, 1H), 3.22 (dd, 1H), 3.64 (s, 3H), 4.10 (m, 1H), 4.18 (d, 1H), 6.87 (d, 2H), 7.76 (m, 1H), 7.80 (dd, 1H)

Ex. erythro-Ibb1081, NMR: 2.86 (dd, 1H), 3.06 (dd, 1H), 3.51 (m, 1H), 3.70 (s, 3H), 4.49 (d, 1H), 6.98 (d, 4H), 7.46 (t, 1H), 8.27 (d, 1H), 8.62 (d, 1H)

Ex. threo-Ibb1081, NMR: 2.90 (m, 2H), 3.60 (s, 3H), 3.65 (q, 1H), 4.12 (d, 1H), 7.03 (m, 4H), 7.62 (t, 1H), 8.22 (d, 1H), 8.62 (d, 1H)

Ex. Iba1082 (erythro-Iba1082:threo-Iba1082=35:65):

erythro-Iba1082, NMR: 2.90 (dd, 1H), 3.10 (dd, 1H), 3.49 (m, 1H), 4.50 (d, 1H), 6.95 (d, 2H), 7.30 (d, 2H), 7.49 (m, 1H)

threo-Iba1082, NMR: 2.93 (m, 2H), 3.64 (q, 1H), 4.14 (d, 1H), 7.05 (d, 2H), 7.27 (d, 2H), 7.65 (m, 1H)

Ex. Ibb1082 (erythro-Ibb1082:threo-Ibb1082=58:42):

erythro-Ibb1082, NMR: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.51 (m, 1H), 3.71 (s, 3H), 4.49 (d, 1H), 6.95 (d, 2H), 7.27 (d, 2H), 7.49 (m, 1H)

threo-Ibb1082, NMR: 2.89 (d, 2H), 3.60 (s, 3H), 3.64 (q, 1H), 4.12 (d, 1H), 7.04 (d, 2H), 7.29 (d, 2H), 7.64 (m, 1H)

Ex. erythro-Ibb1082, NMR: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.51 (m, 1H), 3.71 (s, 3H), 4.49 (d, 1H), 6.95 (d, 2H), 7.27 (d, 2H), 7.49 (m, 1H), 8.27 (d, 1H), 8.62 (d, 1H)

Ex. erythro-1-Ibb1082, NMR: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.51 (m, 1H), 3.71 (s, 3H), 4.49 (d, 1H), 6.95 (d, 2H), 7.27 (d, 2H), 7.49 (m, 1H), 8.27 (d, 1H), 8.62 (d, 1H); chiral HPLC: 28.2 min, mobile phase d

Ex. erythro-2-Ibb1082, NMR: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.51 (m, 1H), 3.71 (s, 3H), 4.49 (d, 1H), 6.95 (d, 2H), 7.27 (d, 2H), 7.49 (m, 1H), 8.27 (d, 1H), 8.62 (d, 1H); chiral HPLC: rt=30.4 min, mobile phase d

Ex. threo-Ibb1082, NMR: 2.89 (d, 2H), 3.60 (s, 3H), 3.64 (q, 1H), 4.12 (d, 1H), 7.04 (d, 2H), 7.29 (d, 2H), 7.64 (m, 1H), 8.22 (d, 1H), 8.63 (d, 1H)

Ex. threo-1-Ibb1082, NMR: 2.89 (d, 2H), 3.60 (s, 3H), 3.64 (q, 1H), 4.12 (d, 1H), 7.04 (d, 2H), 7.29 (d, 2H), 7.64 (t, 1H), 8.22 (d, 1H), 8.63 (d, 1H); chiral HPLC: rt=6.9 min, mobile phase a

Ex. threo-2-Ibb1082, NMR: 2.89 (d, 2H), 3.60 (s, 3H), 3.64 (q, 1H), 4.12 (d, 1H), 7.04 (d, 2H), 7.29 (d, 2H), 7.64 (t, 1H), 8.22 (d, 1H), 8.63 (d, 1H); chiral HPLC: rt=9.9 min, mobile phase a

Ex. Ibc1082 (erythro-Ibc1082:threo-Ibc1082=58:42):

erythro-Ibc1082, NMR: 1.24 (t, 3H), 2.83 (dd, 1H), 3.03 (dd, 1H), 3.51 (m, 1H), 4.14 (q, 2H), 4.48 (d, 1H), 6.95 (d, 2H), 7.28 (d, 2H), 7.49 (m, 1H), 8.27 (m, 1H), 8.63 (m, 1H)

threo-Ibc1082, NMR: 1.16 (t, 3H), 2.89 (d, 2H), 3.63 (q, 1H), 4.03 (m, 2H), 4.12 (d, 1H), 7.04 (d, 2H), 7.26 (d, 2H), 7.64 (m, 1H), 8.22 (m, 1H), 8.63 (m, 1H)

erythro-Ibc1082, NMR: 1.24 (t, 3H), 2.83 (dd, 1H), 3.03 (dd, 1H), 3.51 (m, 1H), 4.14 (q, 2H), 4.48 (d, 1H), 6.95 (d, 2H), 7.28 (d, 2H), 7.49 (m, 1H), 8.27 (m, 1H), 8.63 (m, 1H)

threo-Ibc1082, NMR: 1.16 (t, 3H), 2.89 (d, 2H), 3.63 (q, 1H), 4.03 (m, 2H), 4.12 (d, 1H), 7.04 (d, 2H), 7.26 (d, 2H), 7.64 (m, 1H), 8.22 (m, 1H), 8.63 (m, 1H)

Ex. Ibv1082 (erythro-Ibv1082:threo-Ibv1082=58:42):

erythro-Ibv1082, NMR: 3.09 (t, 2H), 3.47 (m, 1H), 4.28 (t, 2H), 4.47 (d, 1H), 6.93 (d, 2H), 7.49 (t, 1H), 8.28 (d, 1H), 8.63 (d, 1H)

threo-Ibv1082, NMR: 3.02 (t, 2H), 3.59 (q, 1H), 4.12 (d, 1H), 4.16 (m, 2H), 7.01 (d, 2H), 7.67 (t, 1H), 8.21 (d, 1H), 8.63 (d, 1H)

Ex. erythro-Ibb1083, NMR in [D₆-DMSO]: 2.63 (dd, 1H), 2.76 (dd, 1H), 3.39 (s, 3H), 3.75 (m, 1H), 4.75 (d, 1H), 7.28 (d, 2H), 7.57 (d, 2H), 8.11 (t, 1H), 8.50 (d, 1H), 8.72 (d, 1H)

Ex. threo-Ibb1083, NMR in [D₆-DMSO]: 2.94 (m, 2H), 3.45 (s, 3H), 3.85 (m, 1H), 4.74 (d, 1H), 7.18 (d, 2H), 7.46 (d, 2H), 8.06 (t, 1H), 8.33 (d, 1H), 8.61 (d, 1H)

Ex. erythro-Ibb1084, NMR: 2.89 (dd, 1H), 3.10 (dd, 1H), 3.51 (m, 1H), 3.70 (s, 3H), 4.51 (d, 1H), 7.00 (m, 2H), 7.29 (m, 3H), 7.42 (t, 1H), 8.25 (d, 1H), 8.60 (d, 1H)

Ex. threo-Ibb1084, NMR: 2.94 (d, 2H), 3.64 (s, 3H), 3.65 (q, 1H), 4.14 (d, 1H), 7.08 (m, 2H), 7.30 (m, 3H), 7.60 (s, 1H), 8.20 (s, 1H), 8.60 (s, 1H)

Ex. erythro-Ibb1085, NMR: 2.31 (s, 3H), 2.87 (dd, 1H), 3.07 (dd, 1H), 3.48 (m, 1H), 3.70 (s, 3H), 4.47 (d, 1H), 6.87 (d, 2H), 7.08 (d, 2H), 7.44 (m, 1H), 8.23 (d, 1H), 8.60 (d, 1H)

Ex. threo-Ibb1085, NMR: 2.31 (s, 3H), 2.91 (d, 2H), 3.59 (s, 3H), 3.61 (q, 1H), 4.12 (d, 1H), 6.95 (d, 2H), 7.10 (d, 2H), 7.62 (t, 1H), 8.18 (d, 1H), 8.60 (d, 1H)

Ex. erythro-Ibb1087, NMR: 2.90 (dd, 1H), 3.10 (dd, 1H), 3.67 (m, 1H), 3.71 (s, 3H), 4.55 (d, 1H), 7.22 (d, 2H), 7.53 (t, 1H), 8.17 (d, 2H), 8.31 (d, 1H), 8.65 (d, 1H)

Ex. threo-Ibb1087, NMR: 2.97 (d, 2H), 3.60 (s, 3H), 3.79 (q, 1H), 4.19 (d, 1H), 7.33 (d, 2H), 7.69 (t, 1H), 8.20 (d, 2H), 8.26 (bs, 1H), 8.65 (bs, 1H)

Ex. erythro-Ibb1088, NMR: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.47 (m, 1H), 3.70 (s, 3H), 3.78 (s, 3H), 4.46 (d, 1H), 6.80 (d, 2H), 6.91 (d, 2H), 7.44 (s, 1H), 8.25 (s, 1H), 8.60 (s, 1H)

Ex. threo-Ibb1088, NMR: 2.89 (m, 2H), 3.59 (s, 3H), 3.60 (m, 1H), 3.78 (s, 3H), 4.11 (d, 1H), 6.81 (d, 2H), 6.99 (d, 2H), 7.61 (t, 1H), 8.19 (d, 1H), 8.60 (d, 1H)

Ex. erythro-Ibb1089, NMR: 2.87 (dd, 1H), 3.05 (dd, 1H), 3.52 (m, 1H), 3.71 (s, 3H), 4.50 (d, 1H), 6.77 (m, 2H), 7.02 (m, 1H), 7.49 (m, 1H), 8.29 (d, 1H), 8.62 (d, 1H)

Ex. threo-Ibb1089, NMR: 2.92 (d, 2H), 3.61 (s, 3H), 3.65 (q, 1H), 4.13 (d, 1H), 6.83 (m, 1H), 6.88 (d, 1H), 6.99 (m. 1H), 7.65 (m, 1H), 8.23 (d, 1H), 8.62 (d, 1H)

Ex. threo-Ibb1090, NMR: 2.91 (d, 2H), 3.61 (s, 3H), 3.63 (q, 1H), 4.14 (d, 1H), 6.99 (m, 2H), 7.65 (m, 1H), 8.25 (d, 1H), 8.64 (d, 1H)

Ex. erythro-Ibb1092, NMR: 2.28 (s, 3H), 2.87 (dd, 1H), 3.07 (dd, 1H), 3.47 (m, 1H), 3.70 (s, 3H), 4.49 (d, 1H), 6.77 (s, 1H), 6.80 (d, 1H), 7.11 (d, 1H), 7.17 (t, 1H), 7.40 (t, 1H), 8.26 (d, 1H), 8.60 (d, 1H)

Ex. threo-Ibb1092, NMR: 2.28 (s, 3H), 2.91 (d, 2H), 3.60 (s, 3H), 3.61 (q, 1H), 4.14 (d, 1H), 6.87 (m, 2H), 7.09 (d, 1H), 7.19 (t, 1H), 7.59 (t, 1H), 8.21 (d, 1H), 8.61 (d, 1H)

Ex. erythro-Ibb1093, NMR: 2.87 (dd, 1H), 3.06 (dd, 1H), 3.57 (m, 1H), 3.71 (s, 3H), 4.51 (d, 1H), 7.32 (m, 2H), 7.44 (t, 1H), 7.50 (t, 1H), 7.62 (m, 1H), 8.30 (d, 1H), 8.65 (d, 1H)

Ex. threo-Ibb1093, NMR: 2.93 (d, 2H), 3.61 (s, 3H), 3.70 (q, 1H), 4.16 (d, 1H), 7.39 (m, 2H), 7.46 (t, 1H), 7.62 (m, 1H), 7.63 (m, 1H), 8.25 (bs, 1H), 8.66 (bs, 1H)

Ex. erythro-Ibb1094, NMR: 2.90 (dd, 1H), 3.09 (dd, 1H), 3.68 (m, 1H), 3.70 (s, 3H), 4.53 (d, 1H), 7.42 (m, 1H), 7.55 (m, 2H), 7.89 (t, 1H), 8.19 (m, 1H), 8.32 (d, 1H), 8.66 (d, 1H)

Ex. threo-Ibb1094, NMR: 2.98 (d, 2H), 3.61 (s, 3H), 3.80 (q, 1H), 4.21 (d, 1H), 7.51 (m, 2H), 7.68 (t, 1H), 8.00 (t, 1H), 8.17 (m, 1H), 8.26 (d, 1H), 8.65 (d, 1H)

Ex. Ibb1096 (erythro-Ibb1096: threo-Ibb1096=55:45), NMR:

erythro-Ibb1096: 2.83 (dd, 1H), 3.04 (dd, 1H), 3.68 (s, 3H), 3.97 (q, 1H), 4.53 (d, 1H), 7.54 (t, 1H), 8.30 (d, 1H), 8.62 (d, 1H)

threo-Ibb1096: 3.01 (m, 2H), 3.58 (s, 3H), 3.93 (m, 1H), 4.22 (d, 1H), 7.77 (t, 1H), 8.30 (d, 1H), 8.60 (d, 1H)

Ex. erythro-Ibb1103, NMR: 2.84 (dd, 1H), 3.03 (dd, 1H), 3.69 (s, 3H), 3.98 (m, 1H), 4.54 (d, 1H), 7.14 (m, 3H), 7.59 (t, 1H), 8.33 (d, 1H), 8.65 (d, 1H)

Ex. threo-Ibb1103, NMR: 3.00 (m, 2H), 3.59 (s, 3H), 3.97 (m, 1H), 4.20 (d, 1H), 6.91 (m, 1H), 7.13 (m, 2H), 7.80 (t, 1H), 8.34 (d, 1H), 8.64 (d, 1H)

Ex. erythro-Ibb1104, NMR: 2.81 (dd, 1H), 3.01 (dd, 1H), 3.691 (s, 3H), 3.92 (q, 1H), 4.51 (d, 1H), 6.71 (m, 1H), 6.94 (m, 1H), 7.36 (m, 1H), 7.58 (t, 1H), 8.32 (d, 1H), 8.64 (d, 1H)

Ex. threo-Ibb1104, NMR: 2.98 (m, 2H), 3.58 (s, 3H), 3.90 (q, 1H), 4.19 (d, 1H), 6.82 (m, 2H), 7.10 (m, 1H), 7.78 (t, 1H), 8.32 (d, 1H), 8.62 (d, 1H)

Ex. erythro-Ibb1105, NMR: 2.81 (dd, 1H), 2.99 (dd, 1H), 3.71 (s, 3H), 3.95 (q, 1H), 4.53 (d, 1H), 6.92 (m, 1H), 6.99 (m, 1H), 7.10 (m, 1H), 7.60 (m, 1H), 8.36 (d, 1H), 8.66 (d, 1H)

Ex. erythro-1-Ibb1105, NMR: 2.81 (dd, 1H), 2.99 (dd, 1H), 3.69 (s, 3H), 3.94 (q, 1H), 4.53 (d, 1H), 6.92 (m, 1H), 6.99 (m, 1H), 7.10 (m, 1H), 7.60 (t, 1H), 8.35 (d, 1H), 8.65 (d, 1H), chiral HPLC: rt=26.9 min, mobile phase d

Ex. erythro-2-Ibb1105, NMR: 2.81 (dd, 1H), 2.99 (dd, 1H), 3.69 (s, 3H), 3.94 (q, 1H), 4.53 (d, 1H), 6.92 (m, 1H), 6.99 (m, 1H), 7.10 (m, 1H), 7.60 (t, 1H), 8.35 (d, 1H), 8.65 (d, 1H), chiral HPLC: rt=29.2 min, mobile phase d

Ex. threo-Ibb1105, NMR: 2.98 (m, 2H), 3.60 (s, 3H), 3.89 (q, 1H), 4.20 (d, 1H), 6.86 (m, 1H), 7.00 (m, 2H), 7.80 (m, 1H), 8.35 (d, 1H), 8.63 (d, 1H)

Ex. threo-1-Ibb1105, NMR: 2.98 (m, 2H), 3.60 (s, 3H), 3.90 (q, 1H), 4.20 (d, 1H), 6.86 (m, 1H), 7.00 (m, 2H), 7.80 (t, 1H), 8.34 (d, 1H), 8.63 (d, 1H), chiral HPLC: rt=10.9 min, mobile phase c

Ex. threo-2-Ibb1105, NMR: 2.98 (m, 2H), 3.60 (s, 3H), 3.90 (q, 1H), 4.20 (d, 1H), 6.85 (m, 1H), 7.00 (m, 2H), 7.80 (t, 1H), 8.34 (d, 1H), 8.63 (d, 1H), chiral HPLC: rt=15.1 min, mobile phase c

Ex. erythro-Ibb1106, NMR: 2.88 (d, 2H), 3.60 (s, 3H), 4.09 (q, 1H), 4.39 (d, 1H), 6.92 (t, 2H), 7.82 (m, 1H), 8.47 (d, 1H), 8.68 (d, 1H)

Ex. erythro-1-Ibb1106, NMR: 2.88 (d, 2H), 3.60 (s, 3H), 4.09 (q, 1H), 4.39 (d, 1H), 6.92 (t, 2H), 7.83 (m, 1H), 8.47 (d, 1H), 8.69 (d, 1H); chiral HPLC: rt 8.7 min, mobile phase b

Ex. erythro-2-Ibb1106, NMR: 2.88 (d, 2H), 3.60 (s, 3H), 4.09 (q, 1H), 4.39 (d, 1H), 6.92 (t, 2H), 7.83 (m, 1H), 8.47 (d, 1H), 8.69 (d, 1H); chiral HPLC: rt 9.8 min, mobile phase b

Ex. threo-Ibb1106, NMR: 3.12 (dd, 1H), 3.23 (dd, 1H), 3.63 (s, 3H), 4.17 (m, 2H), 6.79 (t, 2H), 7.78 (m, 1H), 8.18 (d, 1H), 8.55 (d, 1H)

Ex. threo-1-Ibb1106, NMR: 3.12 (dd, 1H), 3.23 (dd, 1H), 3.63 (s, 3H), 4.17 (m, 2H), 6.79 (t, 2H), 7.18 (m, 1H), 7.78 (t, 1H), 8.18 (d, 1H), 8.55 (d, 1H); chiral HPLC: rt 7.3 min, mobile phase a

Ex. threo-2-Ibb1106, NMR: 3.12 (dd, 1H), 3.23 (dd, 1H), 3.63 (s, 3H), 4.17 (m, 2H), 6.79 (t, 2H), 7.18 (m, 1H), 7.78 (t, 1H), 8.18 (d, 1H), 8.55 (d, 1H); 7.3 min, chiral HPLC: rt 9.0 min, mobile phase a

Ex. erythro-Ibb1107, NMR: 2.84 (dd, 1H), 3.02 (dd, 1H), 3.50 (m, 1H), 3.71 (s, 3H), 4.48 (d, 1H), 6.74 (m, 1H), 6.91 (m, 1H), 7.09 (m, 1H), 7.53 (t, 1H), 8.30 (d, 1H), 8.64 (d, 1H)

Ex. threo-Ibb1107, NMR: 2.88 (d, 2H), 3.61 (s, 3H), 3.62 (q, 1H), 4.12 (d, 1H), 6.86 (m, 1H), 6.96 (m, 1H), 7.11 (m, 1H), 7.67 (t, 1H), 8.24 (d, 1H), 8.64 (d, 1H)

Ex. threo-Ibb1108, NMR: 2.90 (d, 2H), 3.62 (s, 3H), 3.64 (q, 1H), 4.13 (d, 1H), 6.67 (m, 2H), 6.75 (m. 1H), 7.70 (m, 1H), 8.27 (d, 1H), 8.65 (d, 1H)

Ex. erythro-Ibb1119, NMR: 2.84 (d, 2H), 3.60 (s, 3H), 4.03 (q, 1H), 4.35 (d, 1H), 6.98 (m, 2H), 7.85 (t, 1H), 8.48 (d, 1H), 8.70 (d, 1H)

Ex. threo-Ibb1119, NMR: 3.11 (dd, 1H), 3.21 (dd, 1H), 3.64 (s, 3H), 4.14 (m, 2H), 6.85 (m, 2H), 7.81 (m, 1H), 8.20 (d, 1H), 8.59 (d, 1H)

Ex. erythro-Ibb1123, NMR: 2.84 (dd, 1H), 3.03 (dd, 1H), 3.57 (q, 1H), 3.71 (s, 3H), 4.50 (d, 1H), 7.25 (m, 1H), 7.32 (m, 1H), 7.47 (m, 1H), 7.57 (m, 1H), 8.32 (m, 1H), 8.68 (m, 1H)

Ex. threo-Ibb1123, NMR: 2.90 (d, 2H), 3.61 (s, 3H), 3.69 (q, 1H), 4.15 (d, 1H), 7.34 (d, 1H), 7.45 (s, 1H), 7.50 (dd, 1H), 7.71 (s, 1H), 8.28 (s, 1H), 8.69 (s, 1H)

Ex. Ibb1126 (erythro-Ibb1126: threo-Ibb26=56:44), NMR: erythro-Ibb1126: 2.87 (dd, 1H), 3.07 (dd, 1H), 3.47 (m, 1H), 3.71 (s, 3H), 4.52 (d, 1H), 6.99 (m, 4H), 7.56 (dd, 1H), 7.86 (m, 1H) threo-Ibb1126: 2.90 (m, 2H), 3.61 (s, 3H), 3.64 (q, 1H), 4.15 (d, 1H), 7.04 (m, 4H), 7.72 (dd, 1H), 7.80 (m, 1H)

Ex. threo-Ibb1126: 2.90 (m, 2H), 3.61 (s, 3H), 3.64 (q, 1H), 4.15 (d, 1H), 7.04 (m, 4H), 7.72 (dd, 1H), 7.80 (m, 1H)

Ex. Ibb1127 (erythro-Ibb1 127: threo-Ibb1127=34:66), NMR:

erythro-Ibb1127: 2.86 (dd, 1H), 3.06 (dd, 1H), 3.48 (m, 1H), 3.71 (s, 3H), 4.52 (d, 1H), 6.96 (d, 2H), 7.29 (d, 2H), 7.61 (dd, 1H), 7.86 (m, 1H)

threo-Ibb1127: 2.89 (m, 2H), 3.61 (s, 3H), 3.63 (q, 1H), 4.15 (d, 1H), 7.02 (d, 2H), 7.30 (d, 2H), 7.75 (dd, 1H), 7.81 (m, 1H)

Ex. erythro-Ibb1127: 2.86 (dd, 1H), 3.06 (dd, 1H), 3.48 (m, 1H), 3.71 (s, 3H), 4.52 (d, 1H), 6.96 (d, 2H), 7.29 (d, 2H), 7.61 (dd, 1H), 7.86 (m, 1H)

Ex. threo-Ibb1127: 2.89 (m, 2H), 3.61 (s, 3H), 3.63 (q, 1H), 4.15 (d, 1H), 7.02 (d, 2H), 7.30 (d, 2H), 7.75 (dd, 1H), 7.81 (m, 1H)

Ex. Ibb1128 (erythro-Ibb1128: threo-Ibb1128=68:32), NMR:

erythro-Ibb1128: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.46 (m, 1H), 3.71 (s, 3H), 4.52 (d, 1H), 6.89 (d, 2H), 7.44 (d, 2H), 7.61 (dd, 1H), 7.86 (m, 1H)

threo-Ibb1128: 2.88 (m, 2H), 3.61 (s, 3H), 3.62 (q, 1H), 4.15 (d, 1H), 6.96 (d, 2H), 7.46 (d, 2H), 7.75 (dd, 1H), 7.81 (m, 1H)

Ex. erythro-Ibb1128: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.46 (m, 1H), 3.71 (s, 3H), 4.52 (d, 1H), 6.89 (d, 2H), 7.44 (d, 2H), 7.61 (dd, 1H), 7.86 (m, 1H)

Ex. threo-Ibb1128: 2.88 (m, 2H), 3.61 (s, 3H), 3.62 (q, 1H), 4.15 (d, 1H), 6.96 (d, 2H), 7.46 (d, 2H), 7.75 (dd, 1H), 7.81 (m, 1H)

Ex. Ibb1129 (erythro-Ibb1129: threo-Ibb1129=59:41), NMR: erythro-Ibb1129: 2.90 (dd, 1H), 3.11 (dd, 1H), 3.48 (m, 1H), 3.71 (s, 3H), 4.54 (d, 1H), 6.99 (m, 2H), 7.51 (dd, 1H), 7.84 (m, 1H) threo-Ibb1129: 2.94 (m, 2H), 3.61 (s, 3H), 3.63 (q, 1H), 4.16 (d, 1H), 7.05 (m, 2H), 7.69 (dd, 1H), 7.78 (m, 1H)

Ex. Ibb1131 (erythro-Ibb1131: threo-Ibb1131=40:60), NMR: erythro-Ibb1131: 2.89 (dd, 1H), 3.08 (dd, 1H), 3.57 (m, 1H), 3.72 (s, 3H), 4.56 (d, 1H), 7.17 (d, 2H), 7.63 (m, 3H), 7.89 (m, 1H) threo-Ibb1131: 2.91 (m, 2H), 3.61 (s, 3H), 3.71 (q, 1H), 4.20 (d, 1H), 7.26 (d, 2H), 7.62 (d, 2H), 7.76 (dd, 1H), 7.85 (m, 1H)

Ex. Ibb1132 (erythro-Ibb1132: threo-Ibb1132=34:66), NMR:

erythro-Ibb1132: 2.90 (dd, 1H), 3.10 (dd, 1H), 3.65 (m, 1H), 3.72 (s, 3H), 4.59 (d, 1H), 7.25 (d, 2H), 7.68 (dd, 1H), 7.91 (m, 1H), 8.19 (d, 2H)

threo-Ibb1132: 2.97 (m, 2H), 3.61 (s, 3H), 3.78 (q, 1H), 4.23 (d, 1H), 7.34 (d, 2H), 7.82 (dd, 1H), 7.86 (m, 1H), 8.21 (d, 2H)

Ex. Ibb1133 (erythro-Ibb1133: threo-Ibb1133=57:43), NMR:

erythro-Ibb1133: 2.86 (dd, 1H), 3.07 (dd, 1H), 3.43 (m, 1H), 3.71 (s, 3H), 3.79 (s, 3H), 4.50 (d, 1H), 6.82 (d, 2H), 6.91 (d, 2H), 7.53 (dd, 1H), 7.83 (m, 1H)

threo-Ibb1133: 2.89 (m, 2H), 3.58 (q, 1H), 3.61 (s, 3H), 3.78 (s, 3H), 4.12 (d, 1H), 6.83 (d, 2H), 6.96 (d, 2H), 7.69 (dd, 1H), 7.76 (m, 1H)

Ex. erythro-Ibb1133: 2.86 (dd, 1H), 3.07 (dd, 1H), 3.43 (m, 1H), 3.71 (s, 3H), 3.79 (s, 3H), 4.50 (d, 1H), 6.82 (d, 2H), 6.91 (d, 2H), 7.53 (dd, 1H), 7.83 (m, 1H)

Ex. Ibb1134 (erythro-Ibb1134: threo-Ibb1134=54:46), NMR:

erythro-Ibb1134: 2.87 (dd, 1H), 3.06 (dd, 1H), 3.50 (m, 1H), 3.72 (s, 3H), 4.53 (d, 1H), 7.60 (dd, 1H), 7.89 (d, 1H)

threo-Ibb1134: 2.92 (m, 2H), 3.62 (s, 3H), 3.63 (q, 1H), 4.16 (d, 1H), 7.76 (dd, 1H), 7.82 (d, 1H)

Ex. erythro-Ibb1134: 2.87 (dd, 1H), 3.06 (dd, 1H), 3.50 (m, 1H), 3.72 (s, 3H), 4.53 (d, 1H), 7.60 (dd, 1H), 7.89 (d, 1H)

Ex. erythro-1-Ibb1134: 2.87 (dd, 1H), 3.06 (dd, 1H), 3.50 (m, 1H), 3.72 (s, 3H), 4.53 (d, 1H), 7.60 (dd, 1H), 7.89 (d, 1H)

Ex. erythro-2-Ibb1134: 2.87 (dd, 1H), 3.06 (dd, 1H), 3.50 (m, 1H), 3.72 (s, 3H), 4.53 (d, 1H), 7.60 (dd, 1H), 7.89 (d, 1H)

Ex. threo-Ibb1134: 2.92 (m, 2H), 3.62 (s, 3H), 3.63 (q, 1H), 4.16 (d, 1H), 7.76 (dd, 1H), 7.82 (d, 1H)

Ex. threo-1-Ibb1134: 2.92 (m, 2H), 3.62 (s, 3H), 3.63 (q, 1H), 4.16 (d, 1H), 7.76 (dd, 1H), 7.82 (d, 1H)

Ex. threo-2-Ibb1134: 2.92 (m, 2H), 3.62 (s, 3H), 3.63 (q, 1H), 4.16 (d, 1H), 7.76 (dd, 1H), 7.82 (d, 1H); chiral HPLC: 30.7 min, mobile phase d

Ex. Ibb1139 (erythro-Ibb1139: threo-Ibb1139=37:63), NMR:

erythro-Ibb1139, NMR: 2.90 (dd, 1H), 3.09 (dd, 1H), 3.65 (m, 1H), 3.71 (s, 3H), 4.57 (d, 1H), 7.41 (dt, 1H), 7.53 (t, 1H), 7.68 (dd, 1H), 7.93 (m, 2H), 8.21 (m, 1H)

threo-Ibb1139, NMR: 2.98 (d, 2H), 3.62 (s, 3H), 3.80 (q, 1H), 4.26 (d, 1H), 7.48 (dt, 1H), 7.52 (t, 1H), 7.82 (dd, 1H), 7.88 (m, 1H), 8.02 (m, 1H), 8.20 (m, 1H)

Ex. erythro-Ibb1148, NMR: 2.84 (dd, 1H), 3.05 (dd, 1H), 3.70 (s, 3H), 3.96 (m, 1H), 4.58 (d, 1H), 7.16 (m, 3H), 7.72 (dd, 1H), 7.92 (m, 1H)

Ex. threo-Ibb1148, NMR: 3.02 (m, 2H), 3.60 (s, 3H), 3.96 (q, 1H), 4.22 (d, 1H), 6.90 (m, 1H), 7.06 (m, 1H), 7.13 (m, 1H), 7.93 (m, 2H)

Ex. erythro-Ibb1149, NMR: 2.82 (dd, 1H), 3.04 (dd, 1H), 3.70 (s, 3H), 3.90 (q, 1H), 4.55 (d, 1H), 6.71 (m, 1H), 6.96 (m, 1H), 7.38 (m, 1H), 7.70 (dd, 1H), 7.91 (m, 1H)

Ex. threo-Ibb1149, NMR: 2.99 (m, 2H), 3.60 (s, 3H), 3.88 (q, 1H), 4.20 (d, 1H), 6.82 (m, 2H), 7.10 (m, 1H), 7.91 (m, 2H)

Ex. Ibb1150 (erythro-Ibb1150: threo-Ibb1150=53:47), NMR:

erythro-Ibb1150: 2.81 (dd, 1H), 2.99 (dd, 1H), 3.71 (s, 3H), 3.91 (m, 1H), 4.57 (d, 1H), 6.94 (m, 1H), 7.00 (m, 1H), 7.12 (m, 1H), 7.71 (dd, 1H), 7.93 (m, 1H)

threo-Ibb1150: 2.99 (m, 2H), 3.61 (s, 3H), 3.89 (q, 1H), 4.22 (d, 1H), 6.86 (m, 1H), 7.00 (m, 2H), 7.12 (m, 1H), 7.93 (m, 2H)

Ex. erythro-Ibb1150: 2.81 (dd, 1H), 2.99 (dd, 1H), 3.71 (s, 3H), 3.91 (m, 1H), 4.57 (d, 1H), 6.94 (m, 1H), 7.00 (m, 1H), 7.12 (m, 1H), 7.71 (dd, 1H), 7.93 (m, 1H)

Ex. Ibb1151 (erythro-Ibb1151: threo-Ibb1151=52:48), NMR:

erythro-Ibb1151: 2.88 (dd, 1H), 2.95 (dd, 1H), 3.62 (s, 3H), 4.16 (m, 1H), 4.45 (d, 1H), 6.93 (t, 2H), 7.31 (m, 1H), 7.96 (dd, 1H), 8.07 (m, 1H)

threo-Ibb1151: 3.11 (dd, 1H), 3.23 (dd, 1H), 3.63 (s, 3H), 4.07 (q, 1H), 4.21 (d, 1H), 6.81 (t, 2H), 7.21 (m, 1H), 7.78 (m, 1H), 7.94 (dd, 1H)

Ex. Ibb1152 (erythro-Ibb1152: threo-Ibb1152=63:37), NMR:

erythro-Ibb1152, NMR: 2.83 (dd, 1H), 3.02 (dd, 1H), 3.47 (m, 1H), 3.72 (s, 3H), 4.51 (d, 1H), 6.73 (m, 1H), 6.94 (m, 1H), 7.10 (m, 1H), 7.65 (dd, 1H), 7.90 (m, 1H)

threo-Ibb1152, NMR: 2.88 (d, 2H), 3.61 (q, 1H), 3.62 (s, 3H), 4.15 (d, 1H), 6.82 (m, 1H), 6.96 (m, 1H), 7.11 (m, 1H), 7.77 (dd, 1H), 7.84 (m, 1H)

Ex. erythro-Ibb1152, NMR: 2.83 (dd, 1H), 3.02 (dd, 1H), 3.47 (m, 1H), 3.72 (s, 3H), 4.51 (d, 1H), 6.73 (m, 1H), 6.94 (m, 1H), 7.10 (m, 1H), 7.65 (dd, 1H), 7.90 (m, 1H)

Ex. erythro-Ibb1164: 2.87 (m, 2H), 3.62 (s, 3H), 4.00 (q, 1H), 4.39 (d, 1H), 6.99 (d, 2H), 7.79 (dd, 1H), 8.07 (m, 1H)

Ex. threo-Ibb1164: 3.08 (dd, 1H), 3.22 (dd, 1H), 3.64 (s, 3H), 4.10 (m, 1H), 4.18 (d, 1H), 6.87 (d, 2H), 7.80 (m, 1H), 7.95 (dd, 1H)

Ex. erythro-Ibb1622, NMR: 2.28 (s, 3H), 2.83 (dd, 1H), 3.00 (dd, 1H), 3.52 (m, 1H), 3.67 (s, 3H), 4.40 (d, 1H), 6.95 (d, 2H), 7.15 (t, 1H), 7.24 (d, 2H), 8.19 (bs, 1H), 8.39 (bs, 1H)

Ex. threo-Ibb1622, NMR: 2.33 (s, 3H), 2.89 (d, 2H), 3.58 (s, 3H), 3.64 (q, 1H), 4.10 (d, 1H), 7.04 (d, 2H), 7.27 (d, 2H), 7.29 (t, 1H), 8.14 (d, 1H), 8.39 (d, 1H)

Ex. erythro-Ibb2162, NMR: 2.87 (dd, 1H), 3.11 (dd, 1H), 3.50 (m, 1H), 3.73 (s, 3H), 4.65 (d, 1H), 6.92 (d, 2H), 7.27 (d, 2H), 7.62 (m, 1H), 8.55 (d, 1H), 8.82 (d, 1H)

Ex. threo-Ibb2162, NMR: 2.91 (m, 2H), 3.61 (s, 3H), 3.64 (q, 1H), 4.23 (d, 1H), 7.01 (d, 2H), 7.30 (d, 2H), 7.76 (m, 1H), 8.48 (d, 1H), 8.82 (d, 1H)

Ex. erythro-Ibb2186, NMR: 2.90 (dd, 1H), 3.05 (dd, 1H), 3.66 (s, 3H), 4.10 (m, 1H), 4.58 (d, 1H), 6.90 (t, 2H), 7.33 (m, 1H), 7.90 (t, 1H), 8.75 (d, 1H), 8.87 (d, 1H)

Ex. threo-Ibb2186, NMR: 3.15 (dd, 1H), 3.24 (dd, 1H), 3.64 (s, 3H), 4.17 (m, 1H), 4.27 (d, 1H), 6.80 (t, 2H), 7.21 (m, 1H), 7.85 (t, 1H), 8.50 (d, 1H), 8.76 (d, 1H)

Ex. erythro-Ibb3909, NMR: 2.87 (dd, 1H), 3.02 (dd, 1H), 3.57 (m, 1H), 3.71 (s, 3H), 4.50 (d, 1H), 7.21 (m, 3H), 7.55 (m, 1H), 8.31 (m, 1H), 8.68 (m, 1H)

Ex. threo-Ibb3909, NMR: 2.89 (d, 2H), 3.61 (s, 3H), 3.70 (q, 1H), 4.15 (d, 1H), 7.21 (m, 1H), 7.40 (d, 1H), 8.27 (d, 1H), 8.68 (d, 1H)

Ex. erythro-Ibb3783, NMR: 2.84 (dd, 1H), 3.02 (dd, 1H), 3.46 (m, 1H), 3.70 (s, 3H), 3.87 (s, 3H), 4.46 (d, 1H), 6.69 (m, 1H), 6.80 (dd, 1H), 6.85 (t, 1H), 7.50 (t, 1H), 8.28 (d, 1H), 8.63 (d, 1H)

Ex. threo-Ibb3783, NMR: 2.88 (m, 2H), 3.58 (q, 1H), 3.61 (s, 3H), 3.87 (s, 3H), 4.10 (d, 1H), 6.85 (m, 3H), 7.66 (t, 1H), 8.21 (d, 1H), 8.62 (d, 1H)

Ex. erythro-Ibb3937, NMR: 2.89 (dd, 1H), 3.09 (dd, 1H), 3.60 (m, 1H), 3.71 (s, 3H), 4.53 (d, 1H), 7.15 (d, 2H), 7.47 (m, 1H), 7.56 (d, 2H), 8.30 (bs, 1H), 8.64 (bs, 1H)

Ex. threo-Ibb3937, NMR: 2.94 (m, 2H), 3.60 (s, 3H), 3.74 (q, 1H), 4.17 (d, 1H), 7.26 (d, 2H), 7.59 (d, 2H), 7.64 (t, 1H), 8.26 (d, 1H), 8.64 (d, 1H)

(B) FORMULATION EXAMPLES

-   a) A dust is obtained by mixing 10 parts by weight of a compound of     the formula (I) and 90 parts by weight of talc as inert substance     and comminuting the mixture in a hammer mill. -   b) A wettable powder which is readily dispersible in water is     obtained by mixing 25 parts by weight of a compound of the formula     (I), 64 parts by weight of kaolin-containing quartz as inert     substance, 10 parts by weight of potassium lignosulphonate and 1     part by weight of sodium oleoylmethyltaurate as wetting agent and     dispersant, and grinding the mixture in a pinned-disc mill. -   c) A readily water-dispersible dispersion concentrate is obtained by     mixing 20 parts by weight of a compound of the formula (I) with 6     parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3     parts by weight of isotridecanol polyglycol ether (8 EO) and 71     parts by weight of paraffinic mineral oil (boiling range for example     about 255 to above 277° C.) and grinding the mixture in a ball mill     to a fineness of below 5 microns. -   d) An emulsifiable concentrate is obtained from 15 parts by weight     of a compound of the formula (I), 75 parts by weight of     cyclohexanone as solvent and 10 parts by weight of oxyethylated     nonylphenol as emulsifier. -   e) Water-dispersible granules are obtained by mixing -    75 parts by weight of a compound of the formula (I),     -   10 parts by weight of calcium lignosulphonate,     -   5 parts by weight of sodium laurylsulphate,     -   3 parts by weight of polyvinyl alcohol and     -   7 parts by weight of kaolin, -    grinding the mixture in a pinned-disc mill, and granulating the     powder in a fluidized bed by spray application of water as a     granulating liquid. -   f) Water-dispersible granules are also obtained by homogenizing and     precomminuting -    25 parts by weight of a compound of the formula (I), -    5 parts by weight of sodium     2,2′-dinaphthylmethane-6,6′-disulphonate, -    2 parts by weight of sodium oleoylmethyltaurinate, -    1 part by weight of polyvinyl alcohol, -    17 parts by weight of calcium carbonate and -    50 parts by weight of water, -    on a colloid mill, subsequently grinding the mixture in a bead mill     and atomizing and drying the resulting suspension in a spray tower     by means of a single-substance nozzle.

(C) BIOLOGICAL EXAMPLES 1. Herbicidal Pre-Emergence Action

Seeds of monocotyledonous and dicotyledonous weed plants and crop plants were placed in wood-fibre pots in sandy loam and covered with soil. The compounds (I) according to the invention, formulated in the form of wettable powders (WP), were then applied as aqueous suspension or emulsion at a water application rate of 600 I/ha (converted) with the addition of 0.2% of wetting agent to the surface of the covering soil.

After the treatment, the pots were placed in a greenhouse and kept under good growth conditions for the test plants. After about 3 weeks, the effect of the preparations was scored visually in comparison with untreated controls as percentages. For example, 100% activity=the plants have died, 50% herbicidal activity or damage=the plants have been reduced by 50% or the plant mass has been reduced by 50%, 0% activity=like control plants.

Compounds (I) according to the invention, for example the compounds Nos. erythro-Ibb2, threo-Ibb2, erythro-Ibb9, threo-Ibb9, threo-Ibb10, erythro-Ibb25, threo-Ibb25, erythro-Ibb26, threo-Ibb26, erythro-Ibb542, threo-Ibb542, erythro-Ibb565, threo-Ibb565, erythro-Ibb566, threo-Ibb566, erythro-Ibb1081, threo-Ibb1081, Ibb1082, erythro-Ibb1082, erythro-1-Ibb1082, erythro-2-Ibb1082, threo-Ibb1082, threo-1-Ibb1082, threo-2-Ibb1082, erythro-Ibb1084, threo-Ibb1084, erythro-Ibb1085, threo-Ibb1085, erythro-Ibb1088, threo-Ibb1088, erythro-Ibb1089, threo-Ibb1089, threo-Ibb1090, erythro-Ibb1092, erythro-Ibb1093, threo-Ibb1093, erythro-Ibb1094, threo-Ibb1094, Ibb1096, erythro-Ibb1096, threo-Ibb1096, erythro-Ibb1103, threo-Ibb1103, erythro-Ibb1104, threo-Ibb1104, erythro-Ibb1105, erythro-1-Ibb1105, erythro-2-Ibb1105, threo-Ibb1105, threo-1-Ibb1105, threo-2-Ibb1105, erythro-Ibb1106, erythro-1-Ibb1106, erythro-2-Ibb1106, threo-Ibb1106, threo-1-Ibb1106, threo-2-Ibb1106, erythro-Ibb1107, threo-Ibb1107, threo-Ibb1108, erythro-Ibb1622, threo-Ibb1622, erythro-Ibb3783, threo-Ibb3783 from the above Tables 2 to 2f have good herbicidal activity (70% to 100% activity) against a plurality of harmful plants at an application rate of 320 g or less of active substance per hectare when applied by the pre-emergence method.

Here, for example, the compounds Nos. erythro-Ibb2, threo-Ibb2, threo-Ibb9, threo-Ibb10, erythro-Ibb25, threo-Ibb25, erythro-Ibb26, threo-Ibb26, Ibb1082, threo-Ibb1082, erythro-Ibb1084, threo-Ibb1084, erythro-Ibb1088, threo-Ibb1088, threo-Ibb1089, threo-Ibb1090, threo-Ibb1105, erythro-Ibb1106, threo-Ibb1106 and threo-Ibb1108 have very good activity (90-100%) against harmful plants such as Echinochloa crus-galli when applied by the pre-emergence method at an application rate of 0.32 kg of active substance per hectare.

For example, the compounds Nos. erythro-Ibb2, threo-Ibb2, erythro-Ibb9, threo-Ibb10, erythro-Ibb26, Ibb1082, threo-Ibb1082, threo-Ibb1084, threo-Ibb1088, threo-Ibb1089, threo-Ibb1090, threo-Ibb1105, erythro-Ibb1106, threo-Ibb1106 and threo-Ibb1108 have very good activity (90-100%) against harmful plants such as Setaria virides when applied by the pre-emergence method at an application rate of 0.32 kg of active substance per hectare.

For example, the compounds Nos. erythro-Ibb26, threo-Ibb26, threo-Ibb1089, erythro-Ibb1105, erythro-Ibb1106 and threo-Ibb1106 have very good activity (80-100%) against harmful plants such as Polygonum convolvulus when applied by the pre-emergence method at an application rate of 0.32 kg of active substance per hectare. For example, the compounds Nos. erythro-Ibb9, threo-Ibb9, Ibb1082, threo-Ibb1082, erythro-Ibb1088, threo-Ibb1088, erythro-Ibb1089, threo-Ibb1089, threo-Ibb1090, erythro-Ibb1105, threo-Ibb1105, erythro-Ibb1106, threo-Ibb1106 and threo-Ibb1108 have very good activity (90-100%) against harmful plants such as Veronica persica when applied by the pre-emergence method at an application rate of 0.32 kg of active substance per hectare.

For example, the compounds Nos. erythro-Ibb9, threo-Ibb9, erythro-Ibb26, threo-Ibb26, Ibb1082, threo-Ibb1082, threo-Ibb1084, threo-Ibb1088, erythro-Ibb1105, threo-Ibb1105, erythro-Ibb1106 and threo-Ibb1106 have very good activity (90-100%) against harmful plants such as Viola tricolor when applied by the pre-emergence method at an application rate of 0.32 kg of active substance per hectare.

For example, the compounds Nos. erythro-Ibb2, threo-Ibb2, erythro-Ibb9, threo-Ibb9, threo-Ibb10, erythro-Ibb26, threo-Ibb26, Ibb1082, threo-Ibb1082, erythro-Ibb1088, threo-Ibb1088, threo-Ibb1090, erythro-Ibb1106 and threo-Ibb1106 have very good activity (80-100%) against harmful plants such as Alopecurus myosuroides when applied by the pre-emergence method at an application rate of 0.32 kg of active substance per hectare.

For example, the compounds Nos. erythro-Ibb2, threo-Ibb10, erythro-Ibb26, threo-Ibb26, threo-Ibb1082, erythro-Ibb1105, threo-Ibb1105, erythro-Ibb1106 and threo-Ibb1106 have very good activity (80-100%) against harmful plants such as Amaranthus retroflexus when applied by the pre-emergence method at an application rate of 0.32 kg of active substance per hectare.

2. Herbicidal Post-Emergence Action

Seeds of monocotyledonous and dicotyledonous weeds and crop plants were placed in sandy loam in wood-fibre pots, covered with soil and cultivated in a greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants were treated at the one-leaf stage, where the compounds (I) according to the invention, formulated in the form of wettable powders (WP), were applied by spraying as aqueous suspension or emulsion at a water application rate of 600 I/ha (converted) with the addition of 0.2% of wetting agent to the green parts of the plants. After the test plants had been kept in the greenhouse under optimum growth conditions for about 3 weeks, the activity of the preparations was rated visually in comparison to untreated controls in percent (%). For example, 100% activity=the plants have died, 50% herbicidal activity or damage=the plants have been reduced by 50% or the plant mass has been reduced by 50%, 0% activity=like control plants.

As shown by the results, compounds (I) according to the invention, for example the compounds Nos. erythro-Ibb2, threo-Ibb2, erythro-Ibb9, threo-Ibb9, threo-Ibb10, erythro-Ibb25, threo-Ibb25, erythro-Ibb26, threo-Ibb26, erythro-Ibb542, threo-Ibb542, erythro-Ibb565, threo-Ibb565, erythro-Ibb566, threo-Ibb566, erythro-Ibb1081, threo-Ibb1081, Ibb1082, erythro-Ibb1082, erythro-1-Ibb1082, erythro-2-Ibb1082, threo-Ibb1082, threo-1-Ibb1082, threo-2-Ibb1082, erythro-Ibb1084, threo-Ibb1084, erythro-Ibb1085, threo-Ibb1085, erythro-Ibb1088, threo-Ibb1088, erythro-Ibb1089, threo-Ibb1089, threo-Ibb1090, erythro-Ibb1092, erythro-Ibb1093, threo-Ibb1093, erythro-Ibb1094, threo-Ibb1094, Ibb1096, erythro-Ibb1096, threo-Ibb1096, erythro-Ibb1103, threo-Ibb1103, erythro-Ibb1104, threo-Ibb1104, erythro-Ibb1105, erythro-1-Ibb1105, erythro-2-Ibb1105, threo-Ibb1105, threo-1-Ibb1105, threo-2-Ibb1105, erythro-Ibb1106, erythro-1-Ibb1106, erythro-2-Ibb1106, threo-Ibb1106, threo-1-Ibb1106, threo-2-Ibb1106, erythro-Ibb1107, threo-Ibb1107, threo-Ibb1108, erythro-Ibb1622, threo-Ibb1622, erythro-Ibb3783, threo-Ibb3783 from the above Tables 2 to 2f have good herbicidal activity (70% to 100% activity) against a plurality of harmful plants at an application rate of 320 g or or less of active substance per hectare when applied by the post-emergence method.

Here, for example, the compounds Nos. erythro-Ibb2, threo-Ibb2, threo-Ibb9, threo-Ibb10, erythro-Ibb25, threo-Ibb25, erythro-Ibb26, threo-Ibb26, Ibb1082, threo-Ibb1082, erythro-Ibb1084, threo-Ibb1084, erythro-Ibb1088, threo-Ibb1088, erythro-Ibb1089, threo-Ibb1089, threo-Ibb1090, erythro-Ibb1105, threo-Ibb1105, erythro-Ibb1106, threo-Ibb1106 and threo-Ibb1108 have very good activity (80-100%) against harmful plants such as Echinochloa crus-galli when applied by the post-emergence method at an application rate of 0.32 kg of active substance per hectare.

Here, for example, the compounds Nos. erythro-Ibb2, threo-Ibb2, threo-Ibb9, threo-Ibb10, erythro-Ibb25, threo-Ibb25, erythro-Ibb26, threo-Ibb26, Ibb1082, threo-Ibb1082, erythro-Ibb1084, threo-Ibb1084, threo-Ibb1088, erythro-Ibb1089, threo-Ibb1089, threo-Ibb1090, erythro-Ibb1105, threo-Ibb1105, erythro-Ibb1106, threo-Ibb1106 and threo-Ibb1108 also have very good activity (80-100%) against harmful plants such as Setaria virides when applied by the post-emergence method at an application rate of 0.32 kg of active substance per hectare.

Here, for example, the compounds Nos. erythro-Ibb2, threo-Ibb2, erythro-Ibb9, threo-Ibb9, threo-Ibb10, erythro-Ibb25, threo-Ibb25, erythro-Ibb26, threo-Ibb26, Ibb1082, threo-Ibb1082, erythro-Ibb1084, threo-Ibb1088, erythro-Ibb1089, threo-Ibb1089, threo-Ibb1090, erythro-Ibb1105, threo-Ibb1105, threo-Ibb1106 and threo-Ibb1108 also have very good activity (80-100%) against harmful plants such as Veronica persica when applied by the post-emergence method at an application rate of 0.32 kg of active substance per hectare.

Here, for example, the compounds Nos. erythro-Ibb2, threo-Ibb2, erythro-Ibb9, threo-Ibb9, threo-Ibb10, erythro-Ibb25, threo-Ibb25, erythro-Ibb26, threo-Ibb26, Ibb1082, threo-Ibb1082, threo-Ibb1084, erythro-Ibb1088, threo-Ibb1088, threo-Ibb1090, erythro-Ibb1105, threo-Ibb1105, erythro-Ibb1106, threo-Ibb1106 and threo-Ibb1108 also have very good activity (80-100%) against harmful plants such as Avena fatua when applied by the post-emergence method at an application rate of 0.32 kg of active substance per hectare.

Here, for example, the compounds Nos. erythro-Ibb2, threo-Ibb2, threo-Ibb9, threo-Ibb10, erythro-Ibb25, threo-Ibb25, erythro-Ibb26, threo-Ibb26, Ibb1082, threo-Ibb1082, threo-Ibb1084, threo-Ibb1088, threo-Ibb1090 and threo-Ibb1105 also have very good activity (80-100%) against harmful plants such as Alopecurus myosuroides when applied by the post-emergence method at an application rate of 0.32 kg of active substance per hectare.

Here, for example, the compounds Nos. threo-Ibb10, erythro-Ibb25, threo-Ibb25, erythro-Ibb26, threo-Ibb26, threo-Ibb1082, threo-Ibb1084, erythro-Ibb1105, threo-Ibb1105 and threo-Ibb1108 also have very good activity (80-100%) against harmful plants such as Cyprus esculentus when applied by the post-emergence method at an application rate of 0.32 kg of active substance per hectare.

Here, for example, the compounds Nos. erythro-Ibb2, threo-Ibb26 and threo-Ibb1082 also have very good activity (80-100%) against harmful plants such as Lolium multiflorum when applied by the post-emergence method at an application rate of 0.32 kg of active substance per hectare.

Here, for example, the compounds Nos. erythro-Ibb9 and threo-Ibb26 also have very good activity (80-100%) against harmful plants such as Stellaria media when applied by the post-emergence method at an application rate of 0.32 kg of active substance per hectare.

Here, for example, the compounds Nos. erythro-Ibb2, threo-Ibb2, threo-Ibb9, threo-Ibb25, erythro-Ibb26, threo-Ibb26, threo-Ibb1082, threo-Ibb1084, erythro-Ibb1088, threo-Ibb1088, threo-Ibb1090, erythro-Ibb1105, threo-Ibb1105, erythro-Ibb1106, threo-Ibb1106 and threo-Ibb1108 also have very good activity (80-100%) against harmful plants such as Abutilon theophrasti when applied by the post-emergence method at an application rate of 0.32 kg of active substance per hectare.

Here, for example, the compounds Nos. erythro-Ibb2, threo-Ibb2, threo-Ibb9, erythro-Ibb25, threo-Ibb25, erythro-Ibb26, Ibb1082, threo-Ibb1082, threo-Ibb1084 and erythro-Ibb1105 also have very good activity (80-100%) against harmful plants such as Amaranthus retroflexus when applied by the post-emergence method at an application rate of 0.32 kg of active substance per hectare.

Here, for example, the compounds Nos. threo-Ibb10, erythro-Ibb25, threo-Ibb25, erythro-Ibb26, threo-Ibb26, Ibb1082, threo-Ibb1082, erythro-Ibb1084, threo-Ibb1084, erythro-Ibb1088, threo-Ibb1088, threo-Ibb1090, erythro-Ibb1105, threo-Ibb1105 and threo-Ibb1108 also have very good activity (80-100%) against harmful plants such as Polygonum convolvulus when applied by the post-emergence method at an application rate of 0.32 kg of active substance per hectare.

Here, for example, the compounds Nos. erythro-Ibb2, threo-Ibb2, threo-Ibb9, erythro-Ibb26, threo-Ibb26, Ibb1082, threo-Ibb1090 and threo-Ibb1105 also have very good activity (80-100%) against harmful plants such as Viola tricolor virides when applied by the post-emergence method at an application rate of 0.32 kg of active substance per hectare.

Here, for example, the compounds Nos. erythro-Ibb2, erythro-Ibb26, threo-Ibb26, Ibb1082, threo-Ibb1084, threo-Ibb1088, threo-Ibb1090, threo-Ibb1105 and threo-Ibb1106 also have very good activity (80-100%) against harmful plants such as Pharbitis purpurea when applied by the post-emergence method at an application rate of 0.32 kg of active substance per hectare. 

1. Compound of formula (I) and/or a salt thereof

in which (R¹)_(m) represents m substituents R¹,  where R¹, if m=1, or each of the substituents R¹, if m is greater than 1, independently of the others represents halogen, cyano, nitro, hydroxy, (C₁-C₈)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₁-C₈)-alkoxy, (C₁-C₈)-alkylthio, (C₁-C₈)-alkylsulphinyl, (C₁-C₈)-alkylsulphonyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-haloalkoxy, (C₁-C₆)-haloalkylthio, (C₁-C₆)-haloalkylsulphinyl, (C₁-C₆)-haloalkylsulphonyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl which is optionally substituted by one or more radicals from the group consisting of halogen and (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkoxy which is optionally substituted by one or more radicals from the group consisting of halogen and (C₁-C₄)-alkyl, or a radical of the formula C(O)OR⁵, C(O)NR⁶R⁷, C(O)-Het¹, NR⁸R⁹ or Het² or where in each case two groups R¹ located ortho at the ring or R¹ and R³ together represent a group of the formula —Z¹-A*-Z² in which A* represents an alkylene group having 1 to 4 carbon atoms which is optionally substituted by one or more radicals from the group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy, Z¹ represents a direct bond, O or S and Z² represents a direct bond, O or S,  where the group —Z¹-A*-Z² together with the carbon atoms, attached to the group, of the phenyl ring form a fused-on 5- or 6-membered ring, (R²)_(n) represents n substituents R²,  where R², if n=1, or each of the substituents R², if n is greater than 1, independently of the others represents halogen, cyano, nitro, hydroxy, (C₁-C₈)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₁-C₈)-alkoxy, (C₁-C₈)-alkylthio, (C₁-C₈)-alkylsulphinyl, (C₁-C₈)-alkylsulphonyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-haloalkoxy, (C₁-C₆)-haloalkylthio, (C₁-C₆)-haloalkylsulphinyl, (C₁-C₆)-haloalkylsulphonyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl which is optionally substituted by one or more radicals from the group consisting of halogen and (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkoxy which is optionally substituted by one or more radicals from the group consisting of halogen and (C₁-C₄)-alkyl, or a radical of the formula C(O)OR¹⁰, C(O)NR¹¹R¹², C(O)-Het³, NR¹³R¹⁴ or Het⁴  or where in each case two groups R² located ortho at the ring together are a group of the formula —Z³-A**-Z⁴ in which A** represents an alkylene group having 1 to 4 carbon atoms which is optionally substituted by one or more radicals from the group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy, Z³ represents a direct bond, O or S and Z⁴ represents a direct bond, O or S,  where the group —Z³-A**-Z⁴ together with the carbon atoms, attached to the group, of the phenyl ring form a fused-on 5- or 6-membered ring, R³ represents halogen, cyano, nitro, hydroxy, (C₁-C₈)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₁-C₈)-alkoxy, (C₁-C₈)-alkylthio, (C₁-C₈)-alkylsulphinyl, (C₁-C₈)-alkylsulphonyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-haloalkoxy, (C₁-C₆)-haloalkylthio, (C₁-C₆)-haloalkylsulphinyl, (C₁-C₆)-haloalkylsulphonyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl which is optionally substituted by one or more radicals from the group consisting of halogen and (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkoxy which is optionally substituted by one or more radicals from the group consisting of halogen and (C₁-C₄)-alkyl, or a radical of the formula C(O)OR¹⁵, C(O)NR¹⁶R¹⁷, C(O)-Het⁵, NR¹⁸R¹⁹ or Het⁶ R⁴ represents hydrogen or a hydrolyzable radical, optionally R⁴ represents hydrogen or an optionally substituted hydrocarbon radical or an optionally substituted heterocyclyl radical, where each of the two last-mentioned carbon-containing radicals including substituents has 1 to 30 carbon atoms, optionally 1 to 24 carbon atoms, optionally 1 to 20 carbon atoms,  or R⁴ represents a radical of the formula SiR^(a)R^(b)R^(c), —NR^(a)R^(b) or —N═CR^(c)R^(d), where in the 3 last-mentioned formulae each of the radicals R^(a), R^(b), R^(c) and R^(d) independently of the others represents hydrogen or an optionally substituted hydrocarbon radical, where, however, SiH₃ for SiR^(a)R^(b)R^(c) is excluded, or R^(a) and R^(b) together with the nitrogen atom of the group —NR^(a)R^(b) represent a 3- to 9-membered heterocycle which, in addition to the nitrogen atom, may contain one or two further ring heteroatoms from the group consisting of N, O and S and which is unsubstituted or substituted, or R^(c) and R^(d) together with the carbon atom of the group —N═CR^(C)R^(d) represent a 3- to 9-membered carbocyclic radical or a heterocyclic radical which may contain 1 to 3 ring heteroatoms from the group consisting of N, O and S, where the carbocyclic or heterocyclic radical is unsubstituted or substituted, where each of the radicals R^(a), R^(b), R^(c) and R^(d) including substituents has up to 30 carbon atoms, optionally up to 24 carbon atoms, optionally up to 20 carbon atoms, or R⁴ represents a radical of the formula —C(═O)—R^(e) or —P(═O)(R)₂, where R^(e) and the radicals R^(f) independently of one another each represent hydrogen, OH, (C₁-C₈)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, (C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₈)-alkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkoxy-(C₁-C₈)-alkyl, (C₃-C₈)-alkenyloxy, (C₃-C₈)-alkenyloxy-(C₁-C₈)-alkyl, (C₃-C₈)-alkynyloxy, (C₃-C₈)-alkynyloxy-(C₁-C₈)-alkyl, —NR*R**, with R* and R** being defined below, tri-[(C₁-C₄)-alkyl]silyl, tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₈)alkyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₈)-alkyl, (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkenyl-(C₁-C₈)-alkyl, (C₅-C₆)-cycloalkynyl, (C₅-C₆)-cycloalkynyl-(C₁-C₈)-alkyl, phenyl, phenyl-(C₁-C₈)-alkyl, phenoxy, phenoxy-(C₁-C₈)-alkyl, phenylamino, phenylamino-(C₁-C₈)-alkyl, a radical Het⁷, Het⁷-(C₁-C₆)-alkyl or Het⁷-O—(C₁-C₆)-alkyl, where each of the 15 last-mentioned radicals is unsubstituted in the acyclic moiety or substituted by one or more identical or different radicals R^(A) and is unsubstituted in the cyclic moiety or substituted by one or more identical or different radicals R^(B), R⁵, R¹⁰ and R¹⁵ independently of one another each represent hydrogen, (C₁-C₆)-alkyl, (C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl or the group M mentioned below, optionally (C₁-C₄)-alkyl, R⁶, R⁷, R⁸, R⁹, R¹¹, R¹², R¹³, R¹⁴, R¹⁶, R¹⁷, R¹⁸ and R¹⁹ independently of one another each represent hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, where each of the 3 last-mentioned radicals independently of the others is unsubstituted or substituted by one or more radicals from the group consisting of halogen, nitro, cyano and phenyl which is optionally substituted, optionally unsubstituted or substituted by one or more radicals from the group consisting of halogen, nitro, cyano, (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl, or (C₃-C₆)-cycloalkyl or phenyl, where each of the 2 last-mentioned radicals in each case independently of the other is unsubstituted or substituted by one or more radicals from the group consisting of halogen, nitro, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, phenyl and benzyl, where each of the 2 last-mentioned radicals is optionally substituted, optionally unsubstituted or substituted by one or more radicals from the group consisting of halogen, nitro, cyano, (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl, Het¹, Het², Het³, Het⁴, Het⁵ and Het⁶ independently of one another each represent a saturated or partially unsaturated radical of a heterocycle having 3 to 9 ring atoms and at least one nitrogen atom as ring heteroatom at position 1 of the ring and optionally 1, 2 or 3 further ring heteroatoms from the group consisting of N, O and S, where the radical of the heterocycle at the nitrogen atom in position 1 of the ring is attached to the remainder of the molecule of the compound of the formula (I) and where the heterocycle is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio and oxo, optionally the radical of a saturated heterocycle of the type mentioned, optionally a morpholino, piperidino or pyrrolidino group, Het⁷ independently of the others in each case represents a saturated, partially unsaturated or heteroaromatic monocyclic heterocyclyl radical having 3 to 9 ring atoms or a 9- or 10-membered bicyclic heterocycle, each containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, R*, R** independently of one another (and also independently of other radicals NR*R**) each represent H, (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-alkanoyl, [(C₁-C₄)-haloalkyl]carbonyl, [(C₁-C₄)-alkoxy]carbonyl, [(C₁-C₄)-haloalkoxy]carbonyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl, phenyl, phenyl-(C₁-C₄)-alkyl, where each of the 4 last-mentioned radicals is optionally substituted in the cycle by one or more identical or different radicals from the group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy or, in the case of saturated or partially unsaturated cyclic base groups, also oxo, or R* and R** together with the nitrogen atom represent a 3- to 8-membered heterocycle which, in addition to the nitrogen atom, may contain one or two further ring heteroatoms from the group consisting of N, O and S and which may be unsubstituted or substituted by one or more radicals from the group consisting of (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo, R^(A) represents halogen, cyano, hydroxy or (C₁-C₆)-alkoxy, R^(B) represents halogen, cyano, hydroxy, oxo, nitro, (C₁-C₈)-alkyl, (C₁-C₆)-haloalkyl, cyano-(C₁-C₆)-alkyl, hydroxy-(C₁-C₆)-alkyl, nitro-(C₁-C₆)-alkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-haloalkenyl, (C₂-C₈)-alkynyl, (C₂-C₈)-haloalkynyl, (C₁-C₈)-alkoxy, (C₂-C₈)-alkenyloxy, (C₂-C₈)-alkynyloxy, (C₁-C₈)-haloalkoxy, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkoxy, (C₁-C₈)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₈)-alkylsulphinyl, (C₁-C₆)-haloalkylsulphinyl, (C₁-C₈)-alkylsulphonyl, (C₁-C₆)-haloalkylsulphonyl, a radical of the formula R^(aa)—C(═O)—, R^(aa)—C(═O)—(C₁-C₆)alkyl, the radicals R^(aa) being defined below, —NR*R**, R* and R** being defined below, tri-[(C₁-C₄)-alkyl]silyl, tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₆)-alkyl, (C₃-C₈)-cycloalkyl, (C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkyl, (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkoxy, phenyl, phenyl-(C₁-C₈)-alkyl, phenoxy, phenoxy-(C₁-C₈)-alkyl, phenylamino, phenylamino-(C₁-C₈)-alkyl or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of the 11 last-mentioned radicals is optionally substituted in the cyclic moiety by one or more identical or different radicals R^(bb), R^(aa) independently of one another each represent hydrogen, OH, (C₁-C₈)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, (C₁-C₈)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyloxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkoxy, (C₃-C₈)-alkenyloxy, (C₃-C₈)-alkenyloxy-(C₁-C₆)-alkyl, (C₃-C₈)-alkenyloxy-(C₁-C₆)-alkoxy, (C₃-C₈)-alkynyloxy, (C₃-C₈)-alkynyloxy-(C₁-C₆)-alkyl, (C₃-C₈)-alkynyloxy-(C₁-C₆)-alkoxy, —NR*R*, where R* and R** are as defined above, tri-[(C₁-C₄)alkyl]silyl, tri-[(C₁-C₄)alkyl]silyl-(C₁-C₆)-alkyl, tri-[(C₁-C₄)alkyl]silyl-(C₁-C₆)-alkoxy, (C₃-C₈)-cycloalkyl, (C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkyl, (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkoxy, (C₅-C₈)-cycloalkenyl, (C₅-C₈)-cycloalkenyl-(C₁-C₆)-alkyl, (C₅-C₈)-cycloalkenyloxy, (C₅-C₈)-cycloalkynyl, (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkyl, (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkoxy, phenyl, phenyl-(C₁-C₈)-alkyl, phenyl-(C₁-C₈)-alkoxy, phenoxy, phenoxy-(C₁-C₈)-alkyl, phenoxy-(C₁-C₈)-alkoxy, phenylamino, phenylamino-(C₁-C₈)-alkyl, phenylamino-(C₁-C₈)-alkoxy or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle which is optionally attached via an alkylene group or an alkoxy group and contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of the 20 last-mentioned radicals is optionally substituted in the cyclic moiety by one or more identical or different radicals R^(cc), and R^(bb) and R^(cc) independently of one another each represent halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy or (C₁-C₄)-haloalkoxy or in the case of saturated or partially unsaturated cyclic base groups also represent oxo and M represents an equivalent of a cation, optionally a metal ion equivalent, an ammonium ion which is optionally substituted by 1 to 4 identical or different radicals from the group consisting of (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkynyl, phenyl, (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl, (C₅-C₆)-cycloalkenyl-(C₁-C₄)-alkyl, phenyl-(C₁-C₄)-alkyl, or a tertiary sulphonium ion which is optionally substituted by 3 identical or different radicals from the group consisting of (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkynyl, phenyl, (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl, (C₅-C₆)-cycloalkenyl-(C₁-C₄)-alkyl, phenyl-(C₁-C₄)-alkyl, optionally (C₁-C₄)-alkyl, m represents 0, 1, 2 or 3, optionally 0, 1 or 2, optionally 0 or 1, and n represents 0, 1, 2, 3, 4 or 5, optionally 0, 1, 2 or
 3. 2. Compound and/or salt thereof according to claim 1, wherein R⁴ represents hydrogen or an optionally substituted hydrocarbon radical or an optionally substituted heterocyclyl radical, where each of the two last-mentioned carbon-containing radicals including substituents has 1 to 30 carbon atoms,  or R⁴ represents a radical of the formula SiR^(a)R^(b)R^(c), —NR^(a)R^(b) or —N═CR^(c)R^(d),  where in the 3 last-mentioned formulae each of the radicals R^(a), R^(b), R^(c) and R^(d) independently of the others represents hydrogen or an optionally substituted hydrocarbon radical, where, however, SiH₃ for SiR^(a)R^(b)R^(c) is excluded, or R^(a) and R^(b) together with the nitrogen atom of the group —NR^(a)R^(b) represent a 3- to 9-membered heterocycle which, in addition to the nitrogen atom, may contain one or two further ring heteroatoms from the group consisting of N, O and S and which is unsubstituted or substituted, or R^(c) and R^(d) together with the carbon atom of the group —N═CR^(C)R^(d) represent a 3- to 9-membered carbocyclic radical or a heterocyclic radical which may contain 1 to 3 ring heteroatoms from the group consisting of N, O and S, where the carbocyclic or heterocyclic radical is unsubstituted or substituted, where each of the radicals R^(a), R^(b), R^(c) and R^(d) including substituents has up to 30 carbon atoms,  or R⁴ represents a radical of the formula —C(═O)—R^(e) or —P(═O)(R^(f))₂, where R^(e) and the radicals R^(f) independently of one another each represent hydrogen, OH, (C₁-C₈)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, (C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₈)-alkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkoxy-(C₁-C₈)-alkyl, (C₃-C₈)-alkenyloxy, (C₃-C₈)-alkenyloxy-(C₁-C₈)-alkyl, (C₃-C₈)-alkynyloxy, (C₃-C₈)-alkynyloxy-(C₁-C₈)-alkyl, —NR*R**, with R* and R** being defined below, tri-[(C₁-C₄)-alkyl]silyl, tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₈)alkyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)—cycloalkyl-(C₁-C₈)-alkyl, (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkenyl-(C₁-C₈)-alkyl, (C₅-C₆)-cycloalkynyl, (C₅-C₆)-cycloalkynyl-(C₁-C₈)-alkyl, phenyl, phenyl-(C₁-C₈)-alkyl, phenoxy, phenoxy-(C₁-C₈)-alkyl, phenylamino, phenylamino-(C₁-C₈)-alkyl, a radical Het⁷, Het⁷-(C₁-C₆)-alkyl or Het⁷-O—(C₁-C₆)-alkyl, where each of the 15 last-mentioned radicals is unsubstituted in the acyclic moiety or substituted by one or more identical or different radicals R^(A) and is unsubstituted in the cyclic moiety or substituted by one or more identical or different radicals R^(B), Het⁷ independently of the others in each case represents a saturated, partially unsaturated or heteroaromatic monocyclic heterocyclyl radical having 3 to 9 ring atoms or a 9- or 10-membered bicyclic heterocycle, each containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, R*, R** independently of one another (and also independently of other radicals NR*R**) each represent H, (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-alkanoyl, [(C₁-C₄)-haloalkyl]carbonyl, [(C₁-C₄)-alkoxy]carbonyl, [(C₁-C₄)-haloalkoxy]carbonyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl, phenyl, phenyl-(C₁-C₄)-alkyl, where each of the 4 last-mentioned radicals is optionally substituted in the cycle by one or more identical or different radicals from the group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy or, in the case of saturated or partially unsaturated cyclic base groups, also oxo, or R* and R** together with the nitrogen atom represent a 3- to 8-membered heterocycle which, in addition to the nitrogen atom, may contain one or two further ring heteroatoms from the group consisting of N, O and S and which may be unsubstituted or substituted by one or more radicals from the group consisting of (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo, R^(A) represents halogen, cyano, hydroxy or (C₁-C₆)-alkoxy, R^(B) represents halogen, cyano, hydroxy, oxo, nitro, (C₁-C₈)-alkyl, (C₁-C₆)-haloalkyl, cyano-(C₁-C₆)-alkyl, hydroxy-(C₁-C₆)-alkyl, nitro-(C₁-C₆)-alkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-haloalkenyl, (C₂-C₈)-alkynyl, (C₂-C₈)-haloalkynyl, (C₁-C₈)-alkoxy, (C₂-C₈)-alkenyloxy, (C₂-C₈)-alkynyloxy, (C₁-C₈)-haloalkoxy, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkoxy, (C₁-C₈)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₈)-alkylsulphinyl, (C₁-C₆)-haloalkylsulphinyl, (C₁-C₈)-alkylsulphonyl, (C₁-C₆)-haloalkylsulphonyl, a radical of the formula R^(aa)—C(═O)—, R^(aa)—C(═O)—(C₁-C₆)alkyl, the radicals R^(aa) being defined below, —NR*R**, R* and R** being defined below, tri-[(C₁-C₄)-alkyl]silyl, tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₆)-alkyl, (C₃-C₈)-cycloalkyl, (C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkyl, (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkoxy, phenyl, phenyl-(C₁-C₈)-alkyl, phenoxy, phenoxy-(C₁-C₈)-alkyl, phenylamino, phenylamino-(C₁-C₈)-alkyl or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of the 11 last-mentioned radicals is optionally substituted in the cyclic moiety by one or more identical or different radicals R^(bb), R^(aa) independently of one another each represent hydrogen, OH, (C₁-C₈)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, (C₁-C₈)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyloxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkoxy, (C₃-C₈)-alkenyloxy, (C₃-C₈)-alkenyloxy-(C₁-C₆)-alkyl, (C₃-C₈)-alkenyloxy-(C₁-C₆)-alkoxy, (C₃-C₈)-alkynyloxy, (C₃-C₈)-alkynyloxy-(C₁-C₆)-alkyl, (C₃-C₈)-alkynyloxy-(C₁-C₆)-alkoxy, —NR*R*, where R* and R** are as defined above, tri-[(C₁-C₄)alkyl]silyl, tri-[(C₁-C₄)alkyl]silyl-(C₁-C₆)-alkyl, tri-[(C₁-C₄)alkyl]silyl-(C₁-C₆)-alkoxy, (C₃-C₈)-cycloalkyl, (C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkyl, (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkoxy, (C₅-C₈)-cycloalkenyl, (C₅-C₈)-cycloalkenyl-(C₁-C₆)-alkyl, (C₅-C₈)-cycloalkenyloxy, (C₅-C₈)-cycloalkynyl, (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkyl, (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkoxy, phenyl, phenyl-(C₁-C₈)-alkyl, phenyl-(C₁-C₈)-alkoxy, phenoxy, phenoxy-(C₁-C₈)-alkyl, phenoxy-(C₁-C₈)-alkoxy, phenylamino, phenylamino-(C₁-C₈)-alkyl, phenylamino-(C₁-C₈)-alkoxy or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle which is optionally attached via an alkylene group or an alkoxy group and contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of the 20 last-mentioned radicals is optionally substituted in the cyclic moiety by one or more identical or different radicals R^(cc), and R^(bb) and R^(cc) independently of one another each represent halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy or (C₁-C₄)-haloalkoxy or in the case of saturated or partially unsaturated cyclic base groups also represent oxo.
 3. Compound and/or salt thereof according to claim 1, wherein (R¹)_(m) represents m substituents R¹,  where R¹, if m=1, or each of the substituents R¹, if m is greater than 1, independently of the others represents halogen, cyano, nitro, hydroxy, (C₁-C₆)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, (C₁-C₆)-alkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulphinyl, (C₁-C₆)-alkylsulphonyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulphinyl, (C₁-C₄)-haloalkylsulphonyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-haloalkynyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl which is optionally substituted by one or more radicals from the group consisting of halogen and (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkoxy which is optionally substituted by one or more radicals from the group consisting of halogen and (C₁-C₄)-alkyl, or a radical of the formula C(O)OR⁵, C(O)NR⁶R⁷, C(O)-Het¹, NR⁸R⁹ or Het² or where in each case two groups R¹ located ortho at the ring or R¹ and R³ together represent a group of the formula —Z¹-A*-Z² in which A* represents an alkylene group having 1 to 4 carbon atoms which is optionally substituted by one or more radicals from the group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy, Z¹ represents a direct bond, O or S and Z² represents a direct bond, O or S,  where the group —Z¹-A*-Z² together with the carbon atoms, attached to the group, of the phenyl ring form a fused-on 5- or 6-membered ring, R⁵ represents hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl or the group M, R⁶, R⁷, R⁸ and R⁹ independently of one another each represent hydrogen or (C₁-C₄)-alkyl which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, nitro, cyano and phenyl, or  (C₃-C₆)-cycloalkyl or phenyl, where each of the 2 last-mentioned radicals in each case independently of the other is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, phenyl and benzyl, Het¹ and Het² independently of one another each represent a saturated or partially unsaturated radical of a heterocycle having 3 to 6 ring atoms and at least one nitrogen atom as ring heteroatom at position 1 of the ring and optionally 1, 2 or 3 further ring heteroatoms from the group consisting of N, O and S, where the radical of the heterocycle is attached at the nitrogen atom in position 1 of the ring to the remainder of the molecule of the compound of the formula (I) and where the heterocycle is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo, M represents the equivalent of a cation and m represents 0, 1, 2 or
 3. 4. Compound and/or salt thereof according to claim 1, wherein (R²)_(n) represents n substituents R²,  where R², if n=1, or each of the substituents R², if n is greater than 1, independently of the others represents halogen, cyano, nitro, hydroxy, (C₁-C₆)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, (C₁-C₆)-alkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulphinyl, (C₁-C₆)-alkylsulphonyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulphinyl, (C₁-C₄)-haloalkylsulphonyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-haloalkynyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl which is optionally substituted by one or more radicals from the group consisting of halogen and (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkoxy which is optionally substituted by one or more radicals from the group consisting of halogen and (C₁-C₄)-alkyl, or a radical of the formula C(O)OR¹⁰, C(O)NR¹¹R¹², C(O)-Het³, NR¹³R¹⁴ or Het⁴  or where in each case two groups R² located ortho at the ring together are a group of the formula —Z³-A**-Z⁴ in which A** represents an alkylene group having 1 to 4 carbon atoms which is optionally substituted by one or more radicals from the group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy, Z³ represents a direct bond, O or S and Z⁴ represents a direct bond, O or S,  where the group —Z³-A**-Z⁴ together with the carbon atoms, attached to the group, of the phenyl ring form a fused-on 5- or 6-membered ring, R¹⁰ represents hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl or the group M, R¹¹, R¹², R¹³ and R¹⁴ independently of one another each represent hydrogen or (C₁-C₄)-alkyl which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, nitro, cyano and phenyl, or  (C₃-C₆)-cycloalkyl or phenyl, where each of the 2 last-mentioned radicals in each case independently of the other is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, phenyl and benzyl, Het³ and Het⁴ independently of one another each represent a saturated or partially unsaturated radical of a heterocycle having 3 to 6 ring atoms and at least one nitrogen atom as ring heteroatom at position 1 of the ring and optionally 1, 2 or 3 further ring heteroatoms from the group consisting of N, O and S, where the radical of the heterocycle is attached at the nitrogen atom in position 1 of the ring to the remainder of the molecule of the compound of the formula (I) and where the heterocycle is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo, M represents the equivalent of a cation and n represents 0, 1, 2, 3, 4 or
 5. 5. Compound and/or salt thereof according to claim 1, wherein R³ represents halogen, cyano, nitro, hydroxy, (C₁-C₆)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, (C₁-C₆)-alkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulphinyl, (C₁-C₆)-alkylsulphonyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulphinyl, (C₁-C₄)-haloalkylsulphonyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-haloalkynyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl which is optionally substituted by one or more radicals from the group consisting of halogen and (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkoxy which is optionally substituted by one or more radicals from the group consisting of halogen and (C₁-C₄)-alkyl, or a radical of the formula C(O)OR¹⁵, C(O)NR¹⁶R¹⁷, C(O)-Het⁵, NR¹⁸R¹⁹ or Het⁶, R¹⁵ represents hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl or the group M mentioned, optionally hydrogen, (C₁-C₄)-alkyl or the group M, R¹⁶, R¹⁷, R¹⁸ and R¹⁹ independently of one another each represent hydrogen or (C₁-C₄)-alkyl which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, nitro, cyano and phenyl, or  (C₃-C₆)-cycloalkyl or phenyl, where each of the 2 last-mentioned radicals in each case independently of the other is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, phenyl and benzyl, Het⁵ and Het⁶ independently of one another each represent a saturated or partially unsaturated radical of a heterocycle having 3 to 6 ring atoms and at least one nitrogen atom as ring heteroatom at position 1 of the ring and optionally 1, 2 or 3 further ring heteroatoms from the group consisting of N, O and S, where the radical of the heterocycle is attached at the nitrogen atom in position 1 of the ring to the remainder of the molecule of the compound of the formula (I) and where the heterocycle is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo, and M represents the equivalent of a cation.
 6. Compound and/or salt thereof according to claim 1, wherein (R¹)_(m) represents m substituents R¹,  where R1, if m=1, or each of the substituents R¹, if m is greater than 1, independently of the others represents halogen, cyano, nitro, hydroxy, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl, (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulphinyl, (C₁-C₄)-haloalkylsulphonyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl, or a radical of the formula C(O)OR⁵, C(O)NR⁶R⁷, C(O)-Het¹, NR⁸R⁹ or Het²,  or where in each case two groups R¹ located ortho at the ring or R¹ and R³ together represent a group of the formula —Z¹-A*-Z² in which A* represents an alkylene group having 1 to 4 carbon atoms which is optionally substituted by one or more radicals from the group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy, Z¹ represents a direct bond, O or S and Z² represents a direct bond, O or S,  where the group —Z¹-A*-Z² together with the carbon atoms, attached to the group, of the phenyl ring form a fused-on 5- or 6-membered ring, R⁵ represents hydrogen, (C₁-C₄)-alkyl or the group M mentioned, R⁶, R⁷, R⁸ and R⁹ independently of one another each represent hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, benzyl, (C₃-C₆)-cycloalkyl or phenyl, Het¹ and Het² independently of one another each represent a morpholino, piperidino or pyrrolidino group and m represents 0, 1, 2 or 3, (R²)_(n) represents n substituents R²,  where R², if n=1, or each of the substituents R², if n is greater than 1, independently of one another represent halogen, cyano, nitro, hydroxy, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl, (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulphinyl, (C₁-C₄)-haloalkylsulphonyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl, or a radical of the formula C(O)OR¹⁰, C(O)NR¹¹R¹², C(O)-Het³, NR¹³R¹⁴ or Het⁴,  or where in each case two groups R² located ortho at the ring together are a group of the formula —Z³-A**-Z⁴ in which A** represents an alkylene group having 1 to 4 carbon atoms which is optionally substituted by one or more radicals from the group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy, Z³ represents a direct bond, O or S and Z⁴ represents a direct bond, O or S,  where the group —Z³-A**-Z⁴ together with the carbon atoms, attached to the group, of the phenyl ring form a fused-on 5- or 6-membered ring, R¹⁰ represents hydrogen, (C₁-C₄)-alkyl or the group M mentioned, R¹¹, R¹², R¹³ and R¹⁴ independently of one another each represent hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, benzyl, (C₃-C₆)-cycloalkyl or phenyl, Het³ and Het⁴ independently of one another each represent a morpholino, piperidino or pyrrolidino group and n represents 0, 1, 2, 3, 4 or 5, R³ represents halogen, cyano, nitro, hydroxy, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl, (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulphinyl, (C₁-C₄)-haloalkylsulphonyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl or a radical of the formula C(O)OR¹⁵, C(O)NR¹⁶R¹⁷, C(O)-Het⁵, NR¹⁸R¹⁹ or Het⁶, R¹⁵ represents hydrogen, (C₁-C₄)-alkyl or the group M mentioned, R¹⁶, R¹⁷, R¹⁸ and R¹⁹ independently of one another each represent hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, benzyl, (C₃-C₆)-cycloalkyl or phenyl, Het⁵ and Het⁶ independently of one another each represent a morpholino, piperidino or pyrrolidino group and M represents the equivalent of a cation.
 7. Process for preparing a compound of formula (I) and/or a salt thereof as defined in claim 1 comprising obtaining a, diastereomer mixture of the compound and/or salt of formula (I) comprising the compound (I) to be prepared wherein (a) in the case of preparation of a diastereomer mixture of the compound and/or salt of formula (I), reacting a compound of formula (II)

 with a compound of formula (III) and/or salt thereof

 to give a compound of the formula (I)

 where R¹, R², R³, R⁴, m und n in the compounds (II) and (III) are as defined in the respective compound of the formula (I) to be prepared, and/or (b) compound of the formula (I*)

 in which R is a radical from the group consisting of the radicals possible for R⁴′ but different from the radical R⁴ in the compound (I) to be prepared, is reacted with a compound of formula R⁴—OH in which R⁴ is defined as in formula (I), to give compound (I) and/or salt thereof, where R¹, R², R³, m and n in the compound (I*) are as defined in the compound of the formula (I) to be prepared in each case and/or (c) compound of formula (I*) in which R represents a hydrogen atom is reacted with a compound of formula R⁴—OH in which R⁴ is as defined in formula (I), to give a compound of the formula (I) and/or salt thereof, or (d) in the case in which an optically active compound of a diastereomeric form of the compound of the formula (I) and/or salt is prepared, the racemic mixture of the diastereomeric form of the compound of the formula (I) and/or salt is subjected to an optical resolution and the desired enantiomer is isolated in a stereochemical purity of from 60 to 100%, optionally from 70 to 100%, or optionally from 80 to 100%, in particular or optionally from 90 to 100%, based on the mixture of erythro or threo enantiomers present.
 8. Herbicidal and/or plant growth-regulating composition, comprising one or more compounds of formula (I) and/or salt thereof as defined in claim 1 and one or more formulation auxiliaries customary in crop protection.
 9. Method for controlling harmful plants and/or for regulating growth of a plant, comprising applying an effective amount of one or more compounds of formula (I) and/or salt thereof as defined in claim 1 is applied onto a plant, plant seed, soil in which and/or on which a plant grows and/or an area under cultivation.
 10. Method according to claim 9, that wherein the compound of formula (I) and/or salt thereof is employed for selective control of a harmful plant and/or for regulating growth in a crop of a useful plant and/or ornamental plant.
 11. A compound of formula (I) and/or salt thereof according to claim 1 capable of being used as a herbicide and/or plant growth regulator.
 12. A herbicide and/or plant growth regulator comprising a compound of formula I and/or salt thereof as claimed in claim
 1. 